Triethylamine → ethoxycarbonyl N-(tert-butoxycarbonyl)-S-methylcysteinate

HRID 1504829Notes

Reaction equation

HRID 1504829 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH2:10][S:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:18][C:19](Cl)=[O:20])[CH3:17].C(N(CC)CC)C>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([O:15][C:19]([O:18][CH2:16][CH3:17])=[O:20])=[O:14])[CH2:10][S:11][CH3:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 7018744Boc-cys(ME)-OH

Product 1

HCID 86731709ethoxycarbonyl N-(tert-butoxycarbonyl)-S-methylcysteinate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of N-(tert-butoxycarbonyl)-S-methylcysteine (23.5 g, 0.100 mol) in THF (400 mL) was added dropwise ethylchloroformate (9.6 mL, 0.10 mol) and triethylamine (10.1 g, 0.100 mol) slowly at −10° C. The reaction mixture was stirred at −10° C. for 30 minutes, and then the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give ethoxycarbonyl N-(tert-butoxycarbonyl)-S-methylcysteinate which was used without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e9000d3f83b43d3a06bff4ccc40ff3c
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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