Water → HCID 86646109, compound

HRID 2407510Notes

Reaction equation

HRID 2407510 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[O:22][N:21]=[C:20]([C:23]4[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[CH:25][CH:24]=4)[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(N(CC)CC)C.O>ClCCl>[CH:6]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[O:22][N:21]=[C:20]([C:23]4[CH:28]=[CH:27][C:26]([CH2:29][O:30][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:25][CH:24]=4)[N:19]=3)=[CH:16][CH:17]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59509457HCID 59509457, compound

Product 1

HCID 86646109HCID 86646109, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Methanesulfonyl chloride (0.157 mL, 0.0020 mol) is added to a stirred solution of {4-[5-(4-cyclohexyl phenyl)-[1,2,4]oxadiazole-3-yl]-phenyl}-methanol (0.45 g, 0.0013 mol) and triethylamine (0.376 mL, 0.0027 mol) in dichloromethane (10 mL) at 5° C. Reaction mixture is stirred at 5° C. for 30 minutes, then treated with demineralized water (10 mL). Dichloromethane layer is separated and aqueous layer is extracted with dichloromethane (2×15 mL). Combined organic layer is dried over sodium sulphate and concentrated under reduced pressure to yield methanesulfonic acid 4-[5-(4-cyclohexyl-phenyl)[1,2,4]oxadiazol-3-yl]-benzyl ester.

Workup

  1. customReaction mixture
  2. customDichloromethane layer is separated
  3. extractionaqueous layer is extracted with dichloromethane (2×15 mL)
  4. dry with materialCombined organic layer is dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-011e2adcac59404e832a87d7e62621ec
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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