N-carbobenzyloxyalanine → HCID 86734612, compound

HRID 328087Notes

Reaction equation

HRID 328087 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:18][C:19]1([CH:31]=[CH:30][CH:29]=[CH:28][CH2:27]1)[CH2:20][P:21](=[O:26])([O:24][CH3:25])[O:22][CH3:23]>>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([NH:18][C@@:19]1([CH:27]=[CH:28][CH:29]=[CH:30][CH2:31]1)[CH2:20][P:21](=[O:26])([O:22][CH3:23])[O:24][CH3:25])=[O:16])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 736104N-carbobenzyloxyalanineHCID 86734613HCID 86734613, compound

Product 1

HCID 86734612HCID 86734612, compound

Procedure

In a manner analogous to that given in Example 13 (a), from the N-hydroxysuccinimide ester of N-benzyloxycarbonyl-L-alanine and dimethyl 1-aminobenzylphosphonate hydrochloride, there was obtained an isomeric mixture. After chromatography on silica gel with an isopropanol/ethyl acetate eluant, followed by recrystallization from ethyl acetate/ether, there were isolated dimethyl (1S)-1-[(N-benzyloxycarbonyl-L-alanyl)-amino] -benzylphosphonate of melting point 103°-105° C [[α]D20 =- 46.6°(c = 1% in methanol)]and dimethyl (1R)-1-[(N-benzyl-oxycarbonyl-L-alanyl)]-benzylphosphonate of melting point 120°-122° C [[α]D20 =+ 12.3°(c = 1% in methanol)]

Workup

  1. customthere was obtained an isomeric mixture
  2. customAfter chromatography on silica gel with an isopropanol/ethyl acetate eluant, followed by recrystallization from ethyl acetate/ether

Sources & evidence

ORD record
ord-275003c8cc1847e6bbc0a8ce717aceda
Source dataset
uspto-grants-1977_04
Patent number
US04016148

Reaction notes

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