Water → HCID 178486033, compound

HRID 25641Notes

Reaction equation

HRID 25641 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12](/[CH:15]=[CH:16]/[CH2:17]O)[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].CS([Cl:24])(=O)=O.N1C=CC=CC=1.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12](/[CH:15]=[CH:16]/[CH2:17][Cl:24])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178486039HCID 178486039, compound

Product 1

HCID 178486033HCID 178486033, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4.37 g (16.35 mmol) of trans-(1E)-[4-(3-Hydroxy-propenyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 120 ml CH2Cl2 was treated at 0° C. with 1.4 ml (17.98 mmol) of methanesulfonylchloride, 1.97 ml (24.52 mmol) pyridine and 2 g (16.35 mmol) of DMAP. The reaction mixture was stirred at RT for 3 h, water (5 ml) was added and the reaction was stirred for 5 min. After extraction with aqueous 10% KHSO4/Et2O (3×), the organic phases were washed with aqueous saturated NaHCO3 (2×), aqueous 10% NaCl, dried over Na2SO4 and evaporated to yield 3.51 g (75%) of trans-(1E)-[4-(3-Chloro-propenyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester, mp: 42.5-43.9° C.; MS: 387 (MH+, 1Cl).

Workup

  1. stirringthe reaction was stirred for 5 min
  2. extractionAfter extraction with aqueous 10% KHSO4/Et2O (3×)
  3. washthe organic phases were washed with aqueous saturated NaHCO3 (2×), aqueous 10% NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-45b1f0933e6449899d9231e44f02eaa5
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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