Dimethyl Sulfoxide → HCID 86758058, compound

HRID 1934566Notes

Reaction equation

HRID 1934566 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([N:17]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:18]([O:20][CH2:21][C:22]2([OH:41])[CH:28]([OH:29])[CH2:27][CH2:26][C:25]3[C:30]([O:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][CH:32]=[CH:33][C:24]=3[CH2:23]2)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN(CC)CC>C(Cl)Cl.CCOC(C)=O>[C:42]1([N:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:18]([O:20][CH2:21][C:22]2([OH:41])[C:28](=[O:29])[CH2:27][CH2:26][C:25]3[C:30]([O:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][CH:32]=[CH:33][C:24]=3[CH2:23]2)=[O:19])[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86758059HCID 86758059, compound

Product 1

HCID 86758058HCID 86758058, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of oxalyl chloride (0.052 ml) in CH2Cl2 (10 ml) was added a solution of DMSO (0.084 ml) in CH2Cl2 (0.5 ml) keeping the temperature below −55° C. The mixture was stirred for 20 minutes. After addition of a solution of ethyl {[(6RS,7RS)-6-(N,N-diphenylcarbamoyloxy)methyl-6,7-dihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-yl]oxy}acetate (150 mg) in CH2Cl2 (3 ml) at the same temperature, the mixture was stirred for 30 minutes. After addition of Et3N (0.33 ml), the mixture was warmed to room temperature over 30 minutes. After stirring for 1 hour at the same temperature, the mixture was diluted with EtOAc, washed with 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate solution, water, and then brine. It was dried over magnesium sulfate and then evaporated. The residue was purified by silica gel column chromatography (hexane-EtOAc 5:2) to give ethyl {[6-(N,N-diphenylcarbamoyloxy)methyl-6-hydroxy-7-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-yl]oxy}acetate (97.2 mg) as a solid.

Workup

  1. customthe temperature below −55° C
  2. stirringthe mixture was stirred for 30 minutes
  3. stirringAfter stirring for 1 hour at the same temperature
  4. washwashed with 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate solution, water
  5. dry with materialIt was dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 5:2)

Sources & evidence

ORD record
ord-3a6080720f4842519ab708d19ed86464
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

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