Triethylamine → HCID 15595884, compound

HRID 476985Notes

Reaction equation

HRID 476985 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C@H:5]([CH2:7][S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[NH2:6])[CH3:2].[C:15]([O:19][C:20](=[O:24])[CH:21](Br)[CH3:22])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CN(P(N(C)C)(N(C)C)=O)C>[C:15]([O:19][C:20](=[O:24])[C@H:21]([CH3:22])[NH:6][C@H:5]([C:4]([O:3][CH2:1][CH3:2])=[O:14])[CH2:7][S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 545327tert-Butyl 2-bromopropanoateHCID 57063851S-pentyl-L-cysteine ethyl ester

Product 1

HCID 15595884HCID 15595884, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

In 20 ml of HMPA were dissolved 8.6 g of S-pentyl-L-cysteine ethyl ester and 8.2 g of 2-bromopropionic acid t-butyl ester. To the solution was added 5.5 ml of triethylamine. The solution was stirred at room temperature for 24 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 1:2 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 3.9 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 1:2 mixture of ether and n-hexane as an eluent),

Sources & evidence

ORD record
ord-417a5016568944b1a02c5861a2684bb2
Source dataset
uspto-grants-1989_12
Patent number
US04886813

Reaction notes

Loading…