Chloroform → 11-Benzyloxycarbonyl-6,9-dihydroxy-4-dimethoxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-trien-8-ylmethyl carbamate
Reaction equation
[C:1](=[O:26])([O:3][CH2:4][CH:5]1[C:17]2([OH:19])[O:18][N:12]([CH2:13][CH:14]3[CH:16]2[NH:15]3)[C:11]2[C:6]1=[C:7]([OH:25])[CH:8]=[C:9]([CH:20]([O:23][CH3:24])[O:21][CH3:22])[CH:10]=2)[NH2:2].C(=O)(O)[O-].[Na+].Cl[C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34].C(Cl)(Cl)Cl>O.CO>[C:1](=[O:26])([O:3][CH2:4][CH:5]1[C:17]2([OH:19])[O:18][N:12]([CH2:13][CH:14]3[CH:16]2[N:15]3[C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])[C:11]2[C:6]1=[C:7]([OH:25])[CH:8]=[C:9]([CH:20]([O:23][CH3:24])[O:21][CH3:22])[CH:10]=2)[NH2:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
6,9-Dihydroxy-4-dimethoxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate (22 mg) and sodium bicarbonate (12 mg) were dissolved in water (0.5 ml). To the solution was added benzyl chloroformate (0.02 ml) with stirring in an ice-water bath. The mixture was stirred for 30 minutes in an ice-water bath and subjected to preparative thin layer chromatography. Development was carried out with a mixture of chloroform and methanol to afford 11-benzyloxycarbonyl-6,9-dihydroxy-4-dimethoxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate (15 mg).
Workup
- stirringThe mixture was stirred for 30 minutes in an ice-water bath
Sources & evidence
- ORD record
- ord-f32693a632ca4baba781d72ed4925b3c
- Source dataset
- uspto-grants-1987_02
- Patent number
- US04645765
Reaction notes
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