Methyl chloroformate → HCID 9869777, compound

HRID 720944Notes

Reaction equation

HRID 720944 reaction equation
[CH3:1][N:2]([CH3:29])[S:3]([NH:6][C@@H:7]1[C:13]2[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:12]=2[C:11]2[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[C:21]([O:23][CH3:24])=[CH:22][C:10]=2[CH2:9][CH2:8]1)(=[O:5])=[O:4].Cl[C:31]([O:33][CH3:34])=[O:32].C(N(CC)CC)C>C(#N)C>[C:31](=[O:32])([O:33][CH3:34])[O:18][C:15]1[CH:16]=[CH:17][C:12]2[C:11]3[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[C:21]([O:23][CH3:24])=[CH:22][C:10]=3[CH2:9][CH2:8][C@H:7]([NH:6][S:3]([N:2]([CH3:1])[CH3:29])(=[O:5])=[O:4])[C:13]=2[CH:14]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 58658628HCID 58658628, compound

Product 1

HCID 9869777HCID 9869777, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (5S)-5-{[(dimethylamino)sulphonyl]amino}-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-ol (1) (0.9; 0.71 mmol), methyl chloroformate (0.061 ml; 0.782 mmol) and triethylamine (0.109 ml; 0.782 mmol) in acetonitrile (8 ml) was stirred under argon atmosphere at 40° C. for 4 hours. After evaporation to dryness, the residue was purified by flash chromatography eluting with ethanol/dichloromethane (2/98) to give (5S)-5-{[(dimethylamino)sulphonyl]amino}-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl methyl carbonate.

Workup

  1. customAfter evaporation to dryness
  2. customthe residue was purified by flash chromatography
  3. washeluting with ethanol/dichloromethane (2/98)

Sources & evidence

ORD record
ord-df3e7647c2f043969ef083384fdacd4c
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Reaction notes

Loading…