Trifluoroacetic acid → HCID 57931397, compound

HRID 1516462Notes

Reaction equation

HRID 1516462 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([NH:11][S:12]([C:15]1[C:16]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[C:32]([CH2:33][OH:34])=[C:31]([Cl:35])[N:30]=[C:29]3[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:23][CH:22]=2)=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:14])=[O:13])=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]([NH:11][S:12]([C:15]1[C:16]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[C:32]([CH2:33][OH:34])=[C:31]([Cl:35])[N:30]=[C:29]3[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:23][CH:22]=2)=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:13])=[O:14])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57931398HCID 57931398, compound

Product 1

HCID 57931397HCID 57931397, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a DCM (500 μL) solution of intermediate (1d) (600 mg, 1.0 mmol) was added TFA (500 μL, 6.4 mmol). The mixture was stirred at room temperature for 30 minutes. Volatiles were removed under vacuum and the TFA salt of the product was lyophilized in 50/50 water/acetonitrile to give the title compound as a white solid (418 mg). Anal. HPLC: retention time=1.2 minutes. Gradient conditions: 25% solvent B/75% solvent A to 95% solvent B/5% solvent B over 6 minutes. MS m/z: [M+H]+ calcd for C23H27ClN4O4S, 491.15; found 473.1 [M+H]+−18.

Workup

  1. customVolatiles were removed under vacuum

Sources & evidence

ORD record
ord-d18496caaa874b4692501343f9d6f324
Source dataset
uspto-grants-2012_07
Patent number
US08227497B2

Reaction notes

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