Water → HCID 19897826, compound

HRID 1197156Notes

Reaction equation

HRID 1197156 reaction equation
[CH3:1][N:2]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:3][CH:4]([OH:26])[CH2:5][O:6][C:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:45][S:46](Cl)(=[O:48])=[O:47].O>C(OCC)C.ClCCl>[CH3:1][N:2]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:3][CH:4]([O:26][S:46]([CH3:45])(=[O:48])=[O:47])[CH2:5][O:6][C:7]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 19897834HCID 19897834, compound

Product 1

HCID 19897826HCID 19897826, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

18 g (30 mmol) of 2a was dissolved in 100 ml of dry diethyl ether and 50 ml of dichloromethane. 6.84 g (60 mmol) of methanesulphonyl chloride in 50 ml of dichloromethane was added under stirring, and the mixture was refluxed for 5 hours. Water was then added, and the organic phase was decanted, dried and evaporated. The crude product was chromatographed (eluent as in Step 2), yielding 16.7 g of 3a (80%).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customthe organic phase was decanted
  3. customdried
  4. customevaporated
  5. customThe crude product was chromatographed (eluent as in Step 2)

Sources & evidence

ORD record
ord-5034c8cdb7c1493f9e2e668fdeed44fb
Source dataset
uspto-grants-1992_05
Patent number
US05116992

Reaction notes

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