Trifluoroacetic acid → HCID 86708052, compound

HRID 1524350Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:61])[N:10]([C@@H:16]([CH2:36][CH2:37][CH:38]([F:60])[CH2:39][NH:40]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:17][O:18][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClC(Cl)C>[CH2:1]([O:8][C:9](=[O:61])[N:10]([C@@H:16]([CH2:36][CH2:37][CH:38]([F:60])[CH2:39][NH2:40])[CH2:17][O:18][Si:19]([C:32]([CH3:35])([CH3:33])[CH3:34])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of the material from Step 9 (225 mg, 0.27 mmol) in dichloroethane (1.3 mL) at 0° C. was added trifluoroacetic acid (500 μL, 6.49 mmol). The reaction mixture was stirred at 0° C. for 1 hour, poured into saturated aqueous NaHCO3, and extracted with dichloromethane (2×). The combined organics were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using EtOAc-hexanes to afford 160 mg of the title compound. LCMS (M+1)=593.

Workup

extractionextracted with dichloromethane (2×)
dry with materialThe combined organics were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-4a1f14afa2bc48d0b8766888dd078578
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079834B2

Reaction notes

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