3-(Methoxycarbonyl)-2,2,3-trimethylcyclopentane-1-carboxylic acid → D-Phenylalanine

HRID 1018695Notes

Reaction equation

HRID 1018695 reaction equation
COC(=O)C1(CCC(C(O)=O)C1(C)C)C.Cl.C[O:18][C:19](=[O:40])[C@@H:20]([CH2:22][C:23]1[CH:28]=[CH:27][C:26](NC(=O)C2C(Cl)=CC=CC=2Cl)=[CH:25][CH:24]=1)[NH2:21]>>[NH2:21][C@@H:20]([C:19]([OH:40])=[O:18])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 27367373-(Methoxycarbonyl)-2,2,3-trimethylcyclopentane-1-carboxylic acidHCID 131723645HCID 131723645, compound

Product 1

HCID 71567D-Phenylalanine

Procedure

The preparation follows that of Preparation 37-C-8. The starting materials are (1R-cis)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid 3-methyl ester, 10-A, and 4-[(2,6-dichlorobenzoyl)amino]-D-phenylalanine methyl ester, hydrochloride salt, 37-B-2. Physical properties as follows: m.p.155-159° C.; 1H NMR(300 MHz, DMSO-d6). δ12.4(1H), 10.6(1H), 7.51(5H), 7.19(3H), 4.42(1H), 2.99(2H), 2.64(1H), 2.26(1H), 1.94(1H), 1.68(1H), 1.29(1H), 1.17(3H), 1.05(3H), 0.51(3H) MS−ESI (m/z): 533([M−H−]).

Workup

  1. customThe preparation follows that of Preparation 37-C-8

Sources & evidence

ORD record
ord-d71e8f7e5f834d029bcdc40bb25fb5be
Source dataset
uspto-grants-2002_11
Patent number
US06482849B1

Reaction notes

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