Triethylamine → C15H27NO7S

HRID 56424Notes

Reaction equation

HRID 56424 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH:14]([OH:15])[CH2:13][CH2:12][CH:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH:14]([O:15][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:13][CH2:12][CH:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68616689(1R,3S,4R)-3-(Boc-amino)-4-hydroxy-cyclohexane-carboxylic acid ethyl ester

Product 1

HCID 87507560C15H27NO7SYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Racemate-ethyl 3-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate (12.0 g, 42 mmol) and triethylamine (12.7 g, 126 mmol) in dichloromethane (150 mL) was added methanesulfonyl chloride (9.5 g, 84 mmol) dropwise at 0° C., and the mixture was stirred at 0° C. for 3 hours. The solution was washed with water (100 mL×3) and brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound (15 g, crude) as a yellow oil. MS (ES+) C15H27NO7S requires: 365, found: 266 [M+H−100]+.

Workup

  1. washThe solution was washed with water (100 mL×3) and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ef42b5bfdda84cf98a1e6cef9f34dee5
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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