Propionyl chloride → Ammonia

HRID 479828Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]([CH2:18][NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](Cl)(=[O:29])[CH2:27][CH3:28]>C(Cl)Cl>[NH3:11].[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]([CH2:18][N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26](=[O:29])[CH2:27][CH3:28])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Et(iPr)2N (0.24 mL, 1.38 mmol) was added to a stirring solution of crude 3-phenylaminomethyl-azepane-1-carboxylic acid benzyl ester (148) in CH2Cl2 (2.3 mL) under N2. The reaction was cooled to 0° C. in an ice bath, then propionyl chloride (0.22 mL, 2.53 mmol) was added dropwise. The reaction was allowed to warm to room temperature overnight. The reaction was then judged complete by TLC. It was concentrated in vacuo and EtOAc and 10% NaOH (aq) were added. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo, and purified by automated silica gel chromatography with 96:2:2 Hexanes:CH2Cl2:2N NH3 in EtOH to obtain 3-[(phenyl-propionyl-amino)-methyl]-azepane-1-carboxylic acid benzyl ester (149) (0.3266 g) in 72% yield for two steps.

Workup

temperatureto warm to room temperature overnight
concentrationIt was concentrated in vacuo and EtOAc and 10% NaOH (aq)
additionwere added
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by automated silica gel chromatography with 96:2:2 Hexanes

Sources & evidence

ORD record: ord-5d7f67b1f9f845c298fb9822d55686eb
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06645980B1

Reaction notes

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