Triethylamine → HCID 178454136, compound

HRID 707284Notes

Reaction equation

HRID 707284 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@H:10]([OH:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:12][C@H:10]1[CH2:11][C@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:13])[CH2:9]1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178454126HCID 178454126, compound

Product 1

HCID 178454136HCID 178454136, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl(trans-3-hydroxycyclobutyl)carbamate (20.05 g, 107 mmol, Pharmacore) and triethylamine, anhydrous (22.34 mL, 161 mmol, Sigma-Aldrich Chemical Company, Inc.) in DCM (200 mL) was cooled to −30° C. and methanesulfonyl chloride (9.94 mL, 129 mmol, Sigma-Aldrich Chemical Company, Inc.) was added dropwise over 20 min period. The mixture was stirred at room temperature for 12 h, washed with 200 mL water, then 200 mL 10% aq. citric acid followed by brine, dried over Na2SO4 and evaporated to give the title compound (29 g, 109 mmol, 102% yield), which was used in the next step without further purification.

Workup

  1. washwashed with 200 mL water
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-c1bc6a11a6944eeca5ddf106b124536d
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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