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

HRID 1018694Notes

Reaction equation

HRID 1018694 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 23383932methyl (2S)-2-amino-3-{4-[(2,6-dichlorobenzoyl)amino]phenyl}propionate hydrochloride

Product 1

HCID 6140L-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]-L-phenylalanine methyl ester, hydrochloride salt, 37-B-1. Physical properties as follows: m.p. 154-160° C. 1H NMR(300 MHz, MeOH-d4). δ7.58(2H), 7.42(3H), 7.24(3H), 4.74(1H), 3.3(1H), 3.03(1H), 2.75(1H), 2.41(1H), 2.12(1H), 1.80(1H), 1.43(1H), 1.14(3H), 1.11(3H), 0.63(3H); MS−ESI (m/z): 533([M−H−]); MS−ESI (m/z): 535([M+H+]).

Workup

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

Sources & evidence

ORD record
ord-bf9cba497b5e4d86a9a48da851bd7acf
Source dataset
uspto-grants-2002_11
Patent number
US06482849B1

Reaction notes

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