Triethylamine → HCID 178483636, compound

HRID 967157Notes

Reaction equation

HRID 967157 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][CH2:18][CH2:19][OH:20])[CH2:13][CH2:12]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(N(CC)CC)C>ClCCl>[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][CH2:18][CH2:19][O:20][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:15][CH2:16]1)=[O:21])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178483632HCID 178483632, compound

Product 1

HCID 178483636HCID 178483636, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.35 g (11.20 mmol) trans-{2-[4-(3-hydroxy-propyl)-cyclohexyl]-ethyl}-methyl-carbamic acid tert-butyl ester and 1.54 ml (13.4 mmol) of methanesulfonyl chloride in 35 ml dichloromethane was added under ice-cooling within 5 minutes a solution of 1.87 ml (13.4 mmol) triethylamine in 5 ml of dichloromethane. The reaction mixture was then stirred for 1 hour at room temperature. It was subsequently partitioned between ether, water and 1N hydrogen chloride solution. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure giving 4.06 g (96.1%) almost pure trans-methanesulfonic acid 3-{4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl}-propyl ester as colorless viscous oil, MS: 395 (MNH4+).

Workup

  1. customIt was subsequently partitioned between ether, water and 1N hydrogen chloride solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9fef572f5d69450983188105b65810d6
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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