1,2-Dichloroethane → N-tert-butoxycarbonyl L-methionine cyclopentyl ester

HRID 1251925Notes

Reaction equation

HRID 1251925 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:17]1(O)[CH2:21][CH2:20][CH2:19][CH2:18]1.C(Cl)CCl>CN(C1C=CN=CC=1)C.ClCCl>[CH:17]1([O:15][C:14](=[O:16])[C@H:9]([CH2:10][CH2:11][S:12][CH3:13])[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 7298CyclopentanolHCID 89857Boc-L-methionine

Product 1

HCID 22944441N-tert-butoxycarbonyl L-methionine cyclopentyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-tert-butoxycarbonyl L-methionine (30 g.), cyclopentanol (31 g.), DMAP (44 g.), EDC (30 g.) and dichloromethane (200 ml.) was stirred under an inert atmosphere for 16 hours. It was then washed with 1M. aqueous citric acid (200 ml.), saturated sodium carbonate solution (100 ml.) and brine, dried and evaporated to dryness to give N-tert-butoxycarbonyl L-methionine cyclopentyl ester as a gum(36 g.).

Workup

  1. washIt was then washed with 1M
  2. dry with materialaqueous citric acid (200 ml.), saturated sodium carbonate solution (100 ml.) and brine, dried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-a2ab4aa764cd416c8c7a7784204a4104
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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