Acetic Anhydride → (1-Acetylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate

HRID 2201690Notes

Reaction equation

HRID 2201690 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:23])[O:17][CH2:18][CH:19]1[CH2:22][NH:21][CH2:20]1)([O-:3])=[O:2].[C:24](OC(=O)C)(=[O:26])[CH3:25]>ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:23])[O:17][CH2:18][CH:19]1[CH2:20][N:21]([C:24](=[O:26])[CH3:25])[CH2:22]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 71007325Azetidin-3-ylmethyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 71007323(1-Acetylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of azetidin-3-ylmethyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate (0.35 g, 1.05 mmol, 1 eq.) in dichloromethane (10 mL) was added TEA (0.22 mL, 1.57 mmol, 1.5 eq.) and acetic anhydride (0.11 mL, 1.15 mmol, 1.1 eq.) at 0° C. The reaction was warmed to room temperature and stirred for 1 h. The reaction was diluted with dichloromethane. The organic layer was washed with water and brine. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 4% MeOH/CH2Cl2) to obtain (1-acetylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate (0.31 g, 79% yield).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by column chromatography (silica gel, 4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-de2f979d8fdc4a5f878261bd5d3c4cde
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

Loading…