Water → HCID 178486026, compound

HRID 2209803Notes

Reaction equation

HRID 2209803 reaction equation
[C:1]([O:5][C:6]([N:8]([C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(N(CC)CC)C.O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([C@H:10]1[CH2:11][CH2:12][C@H:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][O:23][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:18][CH:17]=2)[CH2:14][CH2:15]1)[CH3:9])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178486025HCID 178486025, compound

Product 1

HCID 178486026HCID 178486026, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

15.4 g of trans-N-tert.butoxycarbonyl-N-methyl-4-(4-hydroxymethylphenyl)cyclohexylamine in 120 ml of methylene chloride are mixed at O° C. with 4.5 ml of methanesulphonic acid chloride and then 8.1 ml of triethylamine in 20 ml of methylene chloride are slowly added dropwise. After stirring overnight, water is added, the organic phase is washed with water, dried and concentrated by evaporation. After recrystallisation from diisopropylether at low temperature, 12.1 g of the title compound are obtained, melting point 138°-139° C.

Workup

  1. washthe organic phase is washed with water
  2. customdried
  3. concentrationconcentrated by evaporation
  4. customAfter recrystallisation from diisopropylether at low temperature, 12.1 g of the title compound
  5. customare obtained

Sources & evidence

ORD record
ord-a2110ef5423a4f52abaa58ab45c9737d
Source dataset
uspto-grants-1995_10
Patent number
US05455273

Reaction notes

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