Dichloromethane → HCID 178454135, compound

HRID 707378Notes

Reaction equation

HRID 707378 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.C(Cl)Cl.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>O>[CH3:24][S:25]([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:27])=[O:26]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178454125HCID 178454125, compound

Product 1

HCID 178454135HCID 178454135, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a round-bottomed flask charged with tert-butyl(cis-3-hydroxycyclobutyl)carbamate (1.11 g, 5.93 mmol) and triethylamine (2.474 ml, 17.79 mmol) was added CH2Cl2 (12 ml). methanesulfonyl chloride (0.505 ml, 6.52 mmol) was added dropwise via syringe at −20° C. over 5 min. The reaction mixture was stirred at room temperature for 30 min, then diluted with water (15 mL) and extracted with CH2Cl2(2×). The organic extract was washed with saturated NH4Cl and dried over MgSO4. It was filtered and concentrated in vacuo to give cis-3-((tert-butoxycarbonyl)amino)cyclobutyl methanesulfonate (1.64 g, 6.1 mmol, 100% yield) as a off-white solid.

Workup

  1. extractionextracted with CH2Cl2(2×)
  2. extractionThe organic extract
  3. washwas washed with saturated NH4Cl
  4. dry with materialdried over MgSO4
  5. filtrationIt was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17038b38c13f4b7fb034243c82db9113
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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