Trifluoroacetic acid → HCID 11469870, compound

HRID 2427894Notes

Reaction equation

HRID 2427894 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:28])([F:27])[C:10]([NH:12][C:13]([C@@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1C(OC(C)(C)C)=O)=[O:14])=[O:11]>ClCCl>[F:28][C:9]([F:8])([F:27])[C:10]([NH:12][C:13]([C@@H:15]1[CH2:19][CH2:18][CH2:17][NH:16]1)=[O:14])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58991523HCID 58991523, compound

Product 1

HCID 11469870HCID 11469870, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trifluoroacetic acid (14 mL) in 48 mL of dichloromethane was added dropwise in 45 min into a stirring mixture of (S)-tert-butyl 2-(2,2,2-trifluoroacetylcarbamoyl)pyrrolidine-1-carboxylate (1.15 g, 3.70 mmol) and 28 mL of dichloromethane at room temperature. The solution was stirred for 2 h at room temperature, and the volatiles were removed under reduced pressure. The remaining viscous product was treated with ethyl ether (3×20 mL) to provide a white solid in 57% yield. (441 mg, 2.10 mmol). 1H NMR (500 MHz, CD3OD): δ 4.57 (t, 1H, J=7.5 Hz), 3.36-3.24 (m, 2H), 2.39-2.33 (m, 1H), 2.21-2.14 (m, 1H), 2.12-1.97 (m, 2H). 13C NMR (125 MHz, CD3OD): δ 163.5, 163.3, 163.0, 162.7, 121.6, 119.3, 116.9, 116.5, 114.6, 47.9, 47.0, 31.2, 24.5.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. additionThe remaining viscous product was treated with ethyl ether (3×20 mL)
  3. customto provide a white solid in 57% yield

Sources & evidence

ORD record
ord-7866d0b699724b2a95a530566292fc92
Source dataset
uspto-grants-2011_06
Patent number
US07968734B2

Reaction notes

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