Trifluoroacetic acid → Azetidin-3-ylmethyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate

HRID 62680Notes

Reaction equation

HRID 62680 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:18][CH2:19][CH:20]1[CH2:23][N:22](C(OCCCC)=O)[CH2:21]1)=[O:17])([O-:3])=[O:2].C(O)(C(F)(F)F)=O>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:17])[O:18][CH2:19][CH:20]1[CH2:21][NH:22][CH2:23]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712525Butyl 3-((((2-nitro-5-(thiophen-2-yl)phenyl)carbamoyl)oxy)methyl)azetidine-1-carboxylate

Product 1

HCID 71007325Azetidin-3-ylmethyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamateYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tort-butyl 3-((((2-nitro-5-(thiophen-2-yl)phenyl)carbamoyl)oxy)methyl)azetidine-1-carboxylate (0.50 g, 1.15 mmol, 1 eq.) in dichloromethane (10 mL) was added TFA (3 mL) at 0° C. The reaction was stirred at room temperature for 2 h. The reaction was concentrated under reduced pressure. A saturated solution of sodium bicarbonate was added. The obtained solid was filtered and dried under reduced pressure to afford azetidin-3-ylmethyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate (0.35 g, 91% yield).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionA saturated solution of sodium bicarbonate was added
  3. filtrationThe obtained solid was filtered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-bb68253daf194d10a61d3f371f0b759c
Source dataset
uspto-grants-2016_09
Patent number
US09447030B2

Reaction notes

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