Diisopropylethylamine → Benzyl (3,3-difluoroazetidin-1-yl)sulfonylcarbamate

HRID 1525672Notes

Reaction equation

HRID 1525672 reaction equation
[Cl-].[CH2:2]([O:9][C:10]([NH:12][S:13](N1C=CC(=[N+](C)C)C=C1)(=[O:15])=[O:14])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.Cl.[F:35][C:36]1([F:40])[CH2:39][NH:38][CH2:37]1>C(Cl)Cl>[F:35][C:36]1([F:40])[CH2:39][N:38]([S:13]([NH:12][C:10](=[O:11])[O:9][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)(=[O:14])=[O:15])[CH2:37]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 178482961HCID 178482961, compound

Product 1

HCID 89633252Benzyl (3,3-difluoroazetidin-1-yl)sulfonylcarbamateYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(1-(N-((benzyloxy)carbonyl)sulfamoyl)pyridin-4(1H)-ylidene)-N-methylmethanaminium chloride (Preparation 21, 3.15 g, 8.49 mmol) in CH2Cl2 (15 mL) were added N,N,-diisopropylethylamine (2.19 g, 17.0 mmol) and 3,3-difluoroazetidine hydrochloride (1.10 g, 8.49 mmol). The mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the residue diluted with EtOAc (40 mL) and washed with water (40 mL). The aqueous washings were acidified with 2M aqueous solution of HCl and extracted with EtOAC (2×40 mL), the combined organic layers were dried over MgSO4 and concentrated to give the title compound as an amber oil (800 mg, 31%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue diluted with EtOAc (40 mL)
  3. washwashed with water (40 mL)
  4. extractionextracted with EtOAC (2×40 mL)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-530f00f0e6744d248963a9fb6a672182
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

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