Isopropyl 2-hydroxy-2-phenylacetate Pregabalin Impurity

Name: Isopropyl 2-hydroxy-2-phenylacetate Pregabalin Impurity
Brand: ChemScene
Availability: InStock
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CAS No. 4118-51-8
Cat. No. CS-0166145
Purity≥98%
MDL No.MFCD01715837

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Isopropyl 2-hydroxy-2-phenylacetate Pregabalin Impurity|CS-0166145

Structure of 4118-51-8

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General Information

CAS No. 4118-51-8
Cat. No. CS-0166145
Purity ≥98%
MDL No. MFCD01715837
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₄O₃
Molecular Weight 194.23
Synonym(s) Isopropyl mandelate
SMILES O=C(OC(C)C)C(O)C1=CC=CC=C1

Description

Hmb protection of amide bonds has been shown to inhibit aggregation of "difficult" peptides in Fmoc SPPS, thereby leading to products of increased purity [1,2,3,4,5,6]. Retention of Hmb groups on the cleaved peptide can greatly improve the solubility of protected peptide fragments [7,8] and otherwise intractable sequences [9,10,11]. Furthermore, using a Hmb-protected derivative for incorporation of the residue linked to the carboxy group of Asp or Asn residues has been found to suppress formation of aspartimide and piperidide related by-products [12,13,14]. For a comparison of the efficiency of Hmb and pseudoprolines in preventing aggregation, see [15]. Associated Protocols and Technical ArticlesCleavage and Deprotection Protocols for Fmoc SPPSLiterature references[1] T. Johnson, et al. (1993) J. Chem. Soc., Chem. Commun., 369. [2] C. Hyde, et al. (1994) Int. J. Peptide Protein Res., 43, 431. [3] L. C. Packman, et al. (1994) Pept. Res., 7, 125. [4] T. Johnson, et al. (1994) Tetrahedron Lett., 35, 463. [5] R. G. Simmonds (1996) Int. J. Peptide Protein Res., 47, 36. [6] T. Johnson, et al. (1995) Lett. Pept. Sci., 369. [7] M. Quibell, et al. (1995) J. Am. Chem. Soc., 117, 11656. [8] M. Quibell, et al. (1996) J. Chem. Soc., Perkin Trans. 1, 1227. [9] M. Quibell, et al. (1994) Tetrahedron Lett., 35, 2237. [10] M. Quibell, et al. (1994) J. Org. Chem., 59, 1745. [11] M. Quibell, et al. (1995) J. Chem. Soc., Perkin Trans. 1, 2019. [12] M. Quibell, et al. (1994) J. Chem. Soc., Chem. Commun., 2343. [13] L. C. Packman (1995) Tetrahedron Lett., 36, 7523. [14] J. Offer, et al. (1996) J. Chem. Soc., Perkin Trans. 1, 175. [15] W. R. Sampson, et al. (1999) J. Peptide Sci., 5, 403.

Synthesis

Route1
- 31197-66-7
- ~89%
- In-stock
  
  4118-51-8
References
- Sreenivasulu; Arun Kumar; Sateesh Reddy; Siva Kumar; Rajender Kumar; Chandrasekhar; Pal, Manojit Tetrahedron Letters, 2011 , vol. 52, # 6 p. 727 - 732
Route2
- 611-71-2
- 67-63-0
- ~90%
- In-stock
  
  4118-51-8
References
- Houston, Todd A.; Wilkinson, Brendan L.; Blanchfield, Joanne T. Organic Letters, 2004 , vol. 6, # 5 p. 679 - 681
Route3
- In-stock
  
  1074-12-0
- 67-63-0
- ~94%
- In-stock
  
  4118-51-8
References
- Likhar, Pravin R.; Bandyopadhyay, Ananda K. Synlett, 2000 , # 4 p. 538 - 540

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 46.53
LogP 1.6716
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 3

Key Words

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Isopropyl 2-hydroxy-2-phenylacetate Pregabalin Impurity

CAS No. 4118-51-8

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