Hydrochloric Acid → HCID 178483660, compound

HRID 1063646Notes

Reaction equation

HRID 1063646 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][OH:18])[CH2:13][CH2:12]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C.Cl>C(Cl)Cl>[C:1]([O:5][C:6]([N:7]([CH3:8])[CH2:9][CH2:10][C@H:11]1[CH2:12][CH2:13][C@H:14]([CH2:17][O:18][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:15][CH2:16]1)=[O:19])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178483648HCID 178483648, compound

Product 1

HCID 178483660HCID 178483660, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 10 g (36.8 mmol) of trans-[2-(4-hydroxymethyl-cyclohexyl)-ethyl]-methyl-carbamic acid tert-butyl ester in 100 mL of CH2Cl2 were added 3.15 mL (40.5 mmol, 1.3 eq) of methanesulfonyl chloride followed by 6.68 mL (47.9 mmol, 1.3 eq) of triethylamine. Then the reaction mixture was stirred at RT for 1 h. 1M HCl was added, the phases were separated and the inorganic phase was washed with ether. The combined organic phases were washed with water and dried over magnesium sulfate. Concentration of the solution yielded 12.64 g (98%) of trans-methanesulfonic acid 4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexylmethyl ester as colorless oil, MS: 367 (M+NH4+).

Workup

  1. customthe phases were separated
  2. washthe inorganic phase was washed with ether
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-d029d62cae7147b49b29ed64a1ce55e0
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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