Trifluoroacetic acid → (R)-N-((S)-(2-aminothiazol-5-yl)(2-chloro-4-fluorophenyl)methyl)-2-methylpropane-2-sulfinamide

HRID 2043231Notes

Reaction equation

HRID 2043231 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]([NH:23][S:24]([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:25])[C:10]1[S:14][C:13]([NH:15]C(=O)OC(C)(C)C)=[N:12][CH:11]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:15][C:13]1[S:14][C:10]([C@H:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[Cl:1])[NH:23][S@@:24]([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:25])=[CH:11][N:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86621213(R)-tert-Butyl 5-((2-chloro-4-fluorophenyl)(1,1-dimethylethylsulfinamido)methyl)thiazol-2-ylcarbamate

Product 1

HCID 58048512(R)-N-((S)-(2-aminothiazol-5-yl)(2-chloro-4-fluorophenyl)methyl)-2-methylpropane-2-sulfinamideYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-Butyl 5-((2-chloro-4-fluorophenyl)(1,1-dimethylethylsulfinamido)methyl)thiazol-2-ylcarbamate (1.6 g, 3.5 mmol) in CH2Cl2 (6 mL) was added TFA (6 mL). The reaction was stirred at room temperature for 2 h. The TFA and CH2Cl2 were removed under vacuum. The crude product was re-dissolved in CH2Cl2, washed with aqueous NaHCO3 solution, dried over MgSO4 and concentrated. The crude product was recrystallized from EtOAc to provide (R)—N—((S)-(2-aminothiazol-5-yl)(2-chloro-4-fluorophenyl)methyl)-2-methylpropane-2-sulfinamide as colorless solid (672 mg, 53%). 1H NMR (400 MHz, CDCl3) δ 7.56 (dd, J=8.7, 5.9 Hz, 1H), 7.16 (dd, J=8.4, 2.6 Hz, 1H), 7.06 (td, J=8.2, 2.6 Hz, 1H), 6.89 (d, J=0.8 Hz, 1H), 6.07 (d, J=4.6 Hz, 1H), 5.22 (d, J=2.9 Hz, 2H), 4.06 (d, J=4.6 Hz, 1H), 1.28 (s, 9H); HPLC ret. time 2.28 min, 10-99% CH3CN, 5 min run; ESI-MS 362.3 m/z (MH+).

Workup

  1. customThe TFA and CH2Cl2 were removed under vacuum
  2. dissolutionThe crude product was re-dissolved in CH2Cl2
  3. washwashed with aqueous NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was recrystallized from EtOAc

Sources & evidence

ORD record
ord-e06785c068164606a9de382b64bea8dc
Source dataset
uspto-grants-2013_11
Patent number
US08586615B2

Reaction notes

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