Acetic Anhydride → 3-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-5-acetoxy-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH:14]([OH:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:10]1=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30](OC(=O)C)(=[O:32])[CH3:31]>>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH:14]([O:16][C:30](=[O:32])[CH3:31])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:10]1=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
3
Procedure
A solution of 3-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-5-hydroxy-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (described above, 3.0 g) in acetic anhydride (50 ml) was heated at 80° under a dry nitrogen atmosphere for 2 hours. The acetic anhydride was evaporated. The residue was dissolved in ethyl acetate (75 ml) and washed with saturated sodium bicarbonate (50 ml), water (50 ml), and saturated sodium chloride (50 ml). The organic phase was dried (sodium sulfate), evaporated, and the residue triturated with ether (50 ml) to give 3-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-5-acetoxy-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, m.p. 164°-166.5° C. [α]D =-169° (C=0.36 in DMF).
Workup
- customThe acetic anhydride was evaporated
- dissolutionThe residue was dissolved in ethyl acetate (75 ml)
- washwashed with saturated sodium bicarbonate (50 ml), water (50 ml), and saturated sodium chloride (50 ml)
- dry with materialThe organic phase was dried (sodium sulfate)
- customevaporated
- customthe residue triturated with ether (50 ml)
Sources & evidence
- ORD record
- ord-1167db5f3c3f4793be23348ca305b705
- Source dataset
- uspto-grants-1986_03
- Patent number
- US04575503
Reaction notes
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