Acetic Anhydride → Benzyl (1-cyano-3-phenylpropyl)carbamate
Reaction equation
[C:1]([CH:4]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=O)[NH2:2].Cl.N[C@H](C(N)=O)CCC1C=CC=CC=1.C(N1C(=O)CCC1=O)(OCC1C=CC=CC=1)=O.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[C:1]([CH:4]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2]Participants
Conditions
- Temperature
- 75 °C
Procedure
2.78 g of benzyl (1-carbamoyl-3-phenylpropyl)carbamate, prepared from L-homophenylalanine amide hydrochloride and N-Cbz-succinimide, were dissolved in 30 ml of dry pyridine and treated with 6 ml of acetic anhydride. The reaction mixture was stirred at 75° C. for 24 h. The cooled solution was concentrated in vacuo, treated with 100 ml of ethyl acetate, and then extracted three times by shaking with 50 ml each of 5% strength citric acid solution and saturated sodium chloride solution. The organic extract was dried over magnesium sulfate, filtered, concentrated in vacuo, and chromatographed on silica gel using n-heptane/ethyl acetate (1/1). Benzyl (1-cyano-3-phenylpropyl)carbamate was obtained, which was employed in the next stage without further purification.
Workup
- concentrationThe cooled solution was concentrated in vacuo
- additiontreated with 100 ml of ethyl acetate
- extractionextracted three times
- stirringby shaking with 50 ml each of 5% strength citric acid solution and saturated sodium chloride solution
- extractionThe organic extract
- dry with materialwas dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customchromatographed on silica gel
Sources & evidence
- ORD record
- ord-bcd7af2279944b34bd8f897fe6c1606b
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06358978B1
Reaction notes
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