Triethylamine → HCID 54476938, compound

HRID 476988Notes

Reaction equation

HRID 476988 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C@H:5]([CH2:7][S:8][CH2:9][CH2:10][CH3:11])[NH2:6])[CH3:2].[C:13]([O:17][C:18](=[O:22])[CH:19](Br)[CH3:20])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>CN(P(N(C)C)(N(C)C)=O)C>[C:13]([O:17][C:18](=[O:22])[C@H:19]([CH3:20])[NH:6][C@H:5]([C:4]([O:3][CH2:1][CH3:2])=[O:12])[CH2:7][S:8][CH2:9][CH2:10][CH3:11])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 545327tert-Butyl 2-bromopropanoateHCID 57137830HCID 57137830, compound

Product 1

HCID 54476938HCID 54476938, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

In 40 ml of HMPA were dissolved 7.9 g of S-propyl-L-cysteine ethyl ester and 12.4 g of 2-bromopropionic acid t-butyl ester. To the solution was added 8.3 ml of triethylamine, and the mixture was stirred at room temperature for 40 hours. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The extract was sufficiently washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (a 1:3 mixture of ether and n-hexane as an eluent), producing the α-isomer of the title compound as a colorless oil from the first eluate. Yield 4.4 g

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was sufficiently washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (
  6. additiona 1:3 mixture of ether and n-hexane as an eluent),

Sources & evidence

ORD record
ord-67708d01f0be4026b5f44ff222d42571
Source dataset
uspto-grants-1989_12
Patent number
US04886813

Reaction notes

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