Trifluoroacetic acid → HCID 86722616, compound

HRID 587770Notes

Reaction equation

HRID 587770 reaction equation
[S:1]=[C:2]([NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C@H:3]([NH:5]C(=O)OC(C)(C)C)[CH3:4].[C:19]([OH:25])([C:21]([F:24])([F:23])[F:22])=[O:20]>C(Cl)Cl>[F:22][C:21]([F:24])([F:23])[C:19]([O-:25])=[O:20].[S:1]=[C:2]([NH:13][CH2:14][C:15]([F:16])([F:17])[F:18])[C@H:3]([NH3+:5])[CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86722618HCID 86722618, compound

Product 1

HCID 86722616HCID 86722616, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-tert-butyl 1-thioxo-1-(2,2,2-trifluoroethylamino)propan-2-ylcarbamate (200 mg, 0.69 mmol) in CH2Cl2 (5 mL) was added TFA (0.5 mL) dropwise and the reaction mixture was stirred for 18 h. The volatiles were evaporated and the residue was triturated with pentane to give the title compound as colorless gum, which was taken to next step without further purification (200 mg): 1H NMR (300 MHz, DMSO-d6) δ 10.99 (bs, 1H), 8.23 (bs, 2H), 4.62-4.55 (m, 2H), 4.23-4.19 (m, 1H), 1.43 (d, J=8.4 Hz, 3H); ESIMS m/z 186.2 ([M+H]+); IR (thin film) 3445, 2967, 1168 cm−1.

Workup

  1. customThe volatiles were evaporated
  2. customthe residue was triturated with pentane

Sources & evidence

ORD record
ord-0d48907082cd460d81709cc053507b92
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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