Acetic Anhydride → HCID 54045935, compound

HRID 2418738Notes

Reaction equation

HRID 2418738 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][CH2:25][CH3:26])=[O:23])[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28](OC(=O)C)(=[O:30])[CH3:29]>>[C:28]([O:16][CH:14]1[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10](=[O:27])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:15]1)(=[O:30])[CH3:29]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 13604465HCID 13604465, compound

Product 1

HCID 54045935HCID 54045935, compound

Procedure

A solution of 3-(S)-t-butyloxycarbonylamino-1-ethoxycarbonylmethyl-5-hydroxy-2,3,4,5-tetrahydro-1H-[1]benzazepine-2-one (previously described, 1.0 g) in acetic anhydride (20 ml) was maintained at 80° for 3 hours. The reaction mixture was cooled to room temperature and the solvents removed under reduced pressure. Ether (100 ml) was added, and the resulting solution washed with water (50 ml) and dried over magnesium sulfate. The solvent was removed under reduced pressure to give 5-acetoxy-3-(S)-t-butyloxycarbonylamino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one as a pale yellow oil which was used without further purification.

Workup

  1. customthe solvents removed under reduced pressure
  2. additionEther (100 ml) was added
  3. washthe resulting solution washed with water (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8ede712730334f12924669d7aedd78b6
Source dataset
uspto-grants-1984_09
Patent number
US04473575

Reaction notes

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