Phenyl isocyanate → HCID 15051751, compound

HRID 236605Notes

Reaction equation

HRID 236605 reaction equation
[C:1]([N:4]1[CH:16]2[CH:5]1[C:6]1([OH:23])[O:17][N:14]([CH2:15]2)[C:13]2[C:8](=[C:9]([OH:20])[CH:10]=[C:11]([CH:18]=[O:19])[CH:12]=2)[CH:7]1[CH2:21][OH:22])(=[O:3])[CH3:2].[C:24]1([N:30]=[C:31]=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[C:24]1([NH:30][C:31](=[O:32])[O:22][CH2:21][CH:7]2[C:6]3([OH:23])[O:17][N:14]([CH2:15][CH:16]4[CH:5]3[N:4]4[C:1](=[O:3])[CH3:2])[C:13]3[C:8]2=[C:9]([O:20][C:31](=[O:32])[NH:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:10]=[C:11]([CH:18]=[O:19])[CH:12]=3)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 15051750HCID 15051750, compound

Product 1

HCID 15051751HCID 15051751, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 11-acetyl-6,9-dihydroxy-8-hydroxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-triene-4-carbaldehyde (18 mg) in dimethylformamide (1.0 ml) was added a mixture of phenyl isocyanate (12.5 μl) in dimethylformamide (1.25 ml) in an ice-water bath. The mixture was stirred for 30 minutes in an ice-water bath and then stirred for additional 1 hour at ambient temperature. The mixture was evaporated in vacuo and subjected to preparative thin layer chromatography, which was developed with a mixture of chloroform and methanol (15:1, v/v) to afford 11-acetyl-4-formyl-9-hydroxy-6-(N-phenylcarbamoyloxy)-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl N-phenyl-carbamate (12 mg).

Workup

  1. stirringstirred for additional 1 hour at ambient temperature
  2. customThe mixture was evaporated in vacuo
  3. additionwas developed with a mixture of chloroform and methanol (15:1

Sources & evidence

ORD record
ord-9525d156b5ba481b81a41c7c0783cc54
Source dataset
uspto-grants-1987_02
Patent number
US04645765

Reaction notes

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