Trifluoroacetic acid → HCID 67246848, compound

HRID 2425332Notes

Reaction equation

C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:15]=2)[C:10]([CH2:25][C:26]([NH:31][C:32](=[O:34])[CH3:33])([CH2:29][OH:30])[CH2:27][OH:28])=[CH:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:28][CH2:27][C:26]([NH:31][C:32](=[O:34])[CH3:33])([CH2:29][OH:30])[CH2:25][C:10]1[C:11]2[C:16](=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=2)[NH:8][CH:9]=1

Participants

Conditions

Temperature: -40 °C

Procedure

Compound 29 (200 mg, 0.46 mmol) is added to methylene chloride (10 mL) and the solution is cooled to −40° C. Trifluoroacetic acid (3.0 mL) is added and the reaction is stirred for 1 hour maintaining the temperature. The reaction is quenched with methanol (10 mL) at −40° C. and then partitioned between methylene chloride (25 mL) and aqueous sodium hydroxide (1.0 N, 25 mL). The aqueous layer is back extracted with methylene chloride (2×10 mL) and the combined organic layers are washed with aqueous sodium hydroxide (1.0 N, 3×10 mL), then brine and dried over MgSO4. The organic layer is evaporated to dryness and the residue purified using silica gel chromatography with methanol (10%)-methylene chloride (90%) to give compound 30.

Workup

temperaturemaintaining the temperature
customThe reaction is quenched with methanol (10 mL) at −40° C.
custompartitioned between methylene chloride (25 mL) and aqueous sodium hydroxide (1.0 N, 25 mL)
extractionThe aqueous layer is back extracted with methylene chloride (2×10 mL)
washthe combined organic layers are washed with aqueous sodium hydroxide (1.0 N, 3×10 mL)
dry with materialbrine and dried over MgSO4
customThe organic layer is evaporated to dryness
customthe residue purified

Sources & evidence

ORD record: ord-f81d0be8f1ad4ef1938d023b78a2f770
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964649B2

Reaction notes

Loading…