Triethylamine → HCID 178454136, compound

HRID 707266Notes

Reaction equation

HRID 707266 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) and triethylamine, anhydrous (22.34 mL, 161 mmol) in DCM (200 mL) was cooled to −30° C. and methanesulfonyl chloride (9.94 mL, 129 mmol) 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 desired product trans-3-((tert-butoxycarbonyl)amino)cyclobutyl methanesulfonate (29 g, 109 mmol, 102% yield), which was used in the next step without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.03-5.25 (m, 1 H), 4.73 (br. s., 1 H), 4.27 (br. s., 1 H), 3.00 (s, 3 H), 2.67 (ddd, J=13.60, 8.51, 4.50 Hz, 2 H), 2.44 (dt, J=12.86, 6.19 Hz, 2 H), 1.33-1.53 (m, 9 H).

Workup

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

Sources & evidence

ORD record
ord-6f4abf16bfd54eb8b94b83af3ec8c673
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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