Triethylamine → N-Bromoacetyl-S-triphenylmethyl-L-cysteine ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C@H:5]([CH2:7][S:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:6])[CH3:2].C(N(CC)CC)C.[Br:36][CH2:37][C:38](Br)=[O:39]>C1COCC1>[CH2:1]([O:3][C:4](=[O:28])[C@H:5]([CH2:7][S:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH:6][C:38](=[O:39])[CH2:37][Br:36])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of S-triphenylmethyl-L-cysteine ethyl ester (18 g, 46 mmol.) and triethylamine (6.4 mL, 46 mmol.) in dry THF (250 mL) under nitrogen was cooled to 0° C. A solution of bromoacetyl bromide (9.28 g, 46 mmol.) in dry THF (60 mL) was added dropwise during which time the solution turned cloudy. The reaction mixture was stirred at 0° C. for 1 h and then at room temperature for 1 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give an oil. The oil was partitioned between methylene chloride and water (60 mL each), the organic layer washed with 5% HCl, NaHCO3, dried (magnesium sulfate), filtered, and the volatiles removed to give the desired product (69%).
Workup
- waitat room temperature for 1 h
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate was concentrated in vacuo
- customto give an oil
- customThe oil was partitioned between methylene chloride and water (60 mL each)
- washthe organic layer washed with 5% HCl, NaHCO3
- dry with materialdried (magnesium sulfate)
- filtrationfiltered
- customthe volatiles removed
Sources & evidence
- ORD record
- ord-99e1d454d0384ee4a57b68b1ad558de0
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06022523
Reaction notes
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