Methanol → Bz-DL-Ala-CO2Bzl

HRID 1757130Notes

Reaction equation

HRID 1757130 reaction equation
[NH:1]([C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])[C@H:2]([C:4]([OH:6])=O)[CH3:3].[CH2:15]([O:22][CH2:23]C1C=CC=CC=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Na].C(Cl)(Cl)Cl.C[OH:36]>C(O)C1C=CC=CC=1.O>[NH:1]([C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])[CH:2]([C:4]([C:23]([O:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:36])=[O:6])[CH3:3]

Participants

7

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 709778N-benzoyl-L-alanineHCID 66729449CID 66729449

Product 1

HCID 131719092Bz-DL-Ala-CO2BzlYield 26%

Reagents, catalysts & solvents 2

HCID 244Benzyl AlcoholSolventHCID 962WaterSolvent

Procedure

This compound was prepared from Bz-Ala-OH in 26% yield by the procedure described in Example PKC1, except that benzyl oxalyl chloride was used in place of ethyl oxayl chloride and sodium benzyloxide in benzyl alcohol was used for enol ester hydrolysis; single spot on tlc, Rf2 =0.69 (CHCl3 :MeOH=9:1); mp 95°-97° C.; MS, m/e=312 (M+ +1). Anal. Calcd. for C18H17O4N.1/2 H2O: C, 67.48; H, 5.66; N, 4.37. Found: C, 67.78; H, 5.55; N, 4.66.

Sources & evidence

ORD record
ord-abe8778ed88e4248944aae0a7640ab3f
Source dataset
uspto-grants-1995_08
Patent number
US05444042

Reaction notes

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