Trifluoroacetic acid → cyclopentyl (2S)-2-amino-4-(methylsulfanyl)butanoate

HRID 1251926Notes

Reaction equation

HRID 1251926 reaction equation
[CH:1]1([O:6][C:7](=[O:21])[C@H:8]([CH2:17][CH2:18][S:19][CH3:20])[NH:9]C(OC(C)(C)C)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>ClCCl>[CH:1]1([O:6][C:7](=[O:21])[C@H:8]([CH2:17][CH2:18][S:19][CH3:20])[NH2:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22944441N-tert-butoxycarbonyl L-methionine cyclopentyl ester

Product 1

HCID 53747326cyclopentyl (2S)-2-amino-4-(methylsulfanyl)butanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-tert-butoxycarbonyl L-methionine cyclopentyl ester (53 g.), TFA (200 ml.), triethylsilane (39 g.) and dichloromethane (2 L.) was stirred at ambient temperature for 2 hours, evaporated to dryness and then converted to the hydrochloride salt to give L-methionine cyclopentyl ester as a white crystalline solid (40.5 g.).

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-f1463e8ceb3941ee820aa6cd72768d80
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

Loading…