Acetic Anhydride → Methyl 6,9-diacetoxy-11-acetyl-8-carbamoyloxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-4-carboxylate
Reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:28]([O:30][CH3:31])=[O:29])[CH:8]=[C:9]2[C:17]=1[CH:16]([CH2:18][O:19][C:20](=[O:22])[NH2:21])[C:15]1([O:24][C:25](=[O:27])[CH3:26])[O:23][N:10]2[CH2:11][CH:12]2[CH:14]1[NH:13]2)(=[O:3])[CH3:2].[C:32](OC(=O)C)(=[O:34])[CH3:33]>N1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:28]([O:30][CH3:31])=[O:29])[CH:8]=[C:9]2[C:17]=1[CH:16]([CH2:18][O:19][C:20](=[O:22])[NH2:21])[C:15]1([O:24][C:25](=[O:27])[CH3:26])[O:23][N:10]2[CH2:11][CH:12]2[CH:14]1[N:13]2[C:32](=[O:34])[CH3:33])(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 6,9-diacetoxy-8-carbamoyloxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-triene-4-carboxylate (5 mg) in pyridine (1.0 ml) was added acetic anhydride (0.5 ml), and the solution was stirred for 5 hours at room temperature. The reaction mixture was evaporated to dryness in vacuo and the residue was subjected to preparative thin layer chromatography, which was developed with a mixture of chloroform and methanol (30:1, v/v) to afford methyl 6,9-diacetoxy-11-acetyl-8-carbamoyloxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-triene-4-carboxylate (5 mg).
Workup
- customThe reaction mixture was evaporated to dryness in vacuo
- additionwas developed with a mixture of chloroform and methanol (30:1
Sources & evidence
- ORD record
- ord-9aaf14f5d7a74c36abcb696d4ec18cfe
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04861774
Reaction notes
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