Acetic Anhydride → 3-Acetoxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH:14]([CH2:15][OH:16])[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:44](OC(=O)C)(=[O:46])[CH3:45]>ClCCl>[C:1]([O:5][C:6]([CH:8]1[CH:14]([CH2:15][O:16][C:44](=[O:46])[CH3:45])[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-Hydroxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester (0.5 g, 1.25 mmoL) in 6.3 mL dichlormethane was added triethylamine (0.19 mL, 1.38 mmoL) and dimethylaminopyridine (15 mg, 0.125 mmoL). This solution was cooled to 0° C. and acetic anhydride (0.18 ml, 1.88 mmoL) was added in at once. After 5 minutes the reaction was diluted with dichloromethane and washed sequentially with 0.5N HCl, water, and brine. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure to yield 3-Acetoxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester; MS: (M+H)+ =442, (M+NH4)+ =459.
Workup
- washwashed sequentially with 0.5N HCl, water, and brine
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-cf33aee737a042ad8c480308fea79e2d
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06107291
Reaction notes
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