Triethylamine → HCID 178486032, compound

HRID 25594Notes

Reaction equation

HRID 25594 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:22][S:23](Cl)(=[O:25])=[O:24].CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6]([N:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:13][CH2:14]1)=[O:21])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178486030HCID 178486030, compound

Product 1

HCID 178486032HCID 178486032, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.75 g (5.84 mmol) trans-[4-(5-Hydroxy pentyl)-cyclohexyl)-methyl-carbamic acid tert-butyl ester and 0.5 ml (6.42 mmol) of methanesulfonyl chloride in 20 ml CH2Cl2 was added, under cooling with an ice bath, 1.56 ml (11.7 mmol) of Et3N. The mixture was stirred for 3 h at RT. The reaction-mixture was then partitioned between ether/1N HCl and water. The ether-solution was concentrated in vacuo to yield 2.12 g (96%) of clean trans-Methansulfonic acid 5[-4-(tert-butoxy carbonyl-methyl-amino)-cyclohexyl)-pentylester.

Workup

  1. temperatureunder cooling with an ice bath
  2. customThe reaction-mixture was then partitioned between ether/1N HCl and water
  3. concentrationThe ether-solution was concentrated in vacuo

Sources & evidence

ORD record
ord-75456389a7a94295bf690ffcd5899ee7
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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