Azetidine → Benzyl (azetidin-1-ylsulfonyl)carbamate

HRID 1525671Notes

Reaction equation

HRID 1525671 reaction equation
N1CCC1.[Cl-].[CH2:6]([O:13][C:14]([NH:16][S:17]([N:20]1[CH:25]=[CH:24][C:23](=[N+](C)C)C=C1)(=[O:19])=[O:18])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[N:20]1([S:17]([NH:16][C:14](=[O:15])[O:13][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)(=[O:18])=[O:19])[CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 178482961HCID 178482961, compound

Product 1

HCID 89633251Benzyl (azetidin-1-ylsulfonyl)carbamateYield 1,102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Azetidine (0.36 g, 0.5 mmol) was added to N-{1-[N-(benzyloxycarbonyl)-sulfamoyl]pyridin-4(1H)-ylidene}-N-methylmethanaminium chloride (Preparation 21, 2.0 g, 0.5 mmol) in DCM (10 mL). The reaction mixture was stirred overnight at room temperature. The mixture was concentrated in vacuo and the residue partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was discarded and the aqueous layer was acidified with 1M HCl. The aqueous layer was extracted with ethylacetate (2×50 mL), dried over magnesium sulfate and concentrated to afford the title compound (1.49 g, 100%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. extractionThe aqueous layer was extracted with ethylacetate (2×50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9aaf321f7d2f4962a86df03130dc5cc3
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

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