Water → HCID 178484027, compound

HRID 967217Notes

Reaction equation

HRID 967217 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]#[C:17][CH2:18][OH:19])[CH2:12][CH2:11]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:21][S:22](Cl)(=[O:24])=[O:23].N1C(C)=CC=CC=1C.O>C(Cl)Cl>[C:1]([O:5][C:6]([N:7]([CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]#[C:17][CH2:18][O:19][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:12][CH2:11]1)[CH3:8])=[O:20])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-Lutidine2×HCID 31297Methanesulfonyl chloride2×HCID 178484020HCID 178484020, compound

Product 1

HCID 178484027HCID 178484027, compoundYield 119.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8.16 g (29 mmol) of trans-[4-(3-hydroxy-prop-1-ynyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester in 230 ml methylenechloride was treated at 0° C. with 2.48 ml (31.9 mmol) of methanesulfonylchloride and 5.05 ml (43.5 mmol) of 2,6-lutidine. The reaction mixture was stirred over night to room temperature. The reaction was cooled (0° C.) and treated again with 0.68 ml (8.7 mmol) of methanesulfonylchloride and 1.68 ml (14.5 mmol) of 2,6-lutidine and stirred for 24 hours. Water (35 ml) was added and the reaction was stirred for 5 minutes. After extraction with aqueous saturated NaHCO3/ether (3×), the organic phases were washed with aqueous 10% NaCl, dried over sodium sulfate and evaporated to yield 12.5 g of crude trans-methanesulfonic acid 3-{4-[(tert-butoxycarbonyl-methyl-amino)-methyl]-cyclohexyl}-prop-2-ynyl ester as brown oil, MS: 360 (MH+).

Workup

  1. temperatureThe reaction was cooled (0° C.)
  2. stirringstirred for 24 hours
  3. stirringthe reaction was stirred for 5 minutes
  4. extractionAfter extraction with aqueous saturated NaHCO3/ether (3×)
  5. washthe organic phases were washed with aqueous 10% NaCl
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-ad62782fa9ad4c9da928a827a2044356
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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