Trifluoroacetic acid → HCID 11454316, compound

HRID 2118215Notes

Reaction equation

[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13](/[C:16](/[C:26]2[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[C:34]([O:36]C(C)(C)C)=[O:35])=[CH:28][CH:27]=2)=[C:17](\[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)/[CH2:18][CH3:19])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13](/[C:16](/[C:26]2[CH:27]=[CH:28][C:29](/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35])=[CH:30][CH:31]=2)=[C:17](\[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)/[CH2:18][CH3:19])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 19 was dissolved in CH2Cl2 (10 mL) and cooled to 0° C. in an ice bath. TFA (5 mL, 65 mmol) was and the mixture stirred in an ice bath for 2 h. The reaction was concentrated at RT and dried under high vacuum to provide the title compound, 18, as a white solid (53 mg, 74%). 1HNMR (400 MHz, DMSO-d6): δ 0.86 (t, 3H), 2.40 (q, 2H), 6.51 (d, J=16 Hz, 1H), 6.90 (d, J=8 Hz, 2H), 6.96 (d, J=8 Hz, 2H), 7.14-7.18 (m, 3H), 7.16-7.20 (m, 4H), 7.54 (d, J=8 Hz, 2H), 7.56 (d, J=16 Hz, 1H), 7.66-7.71 (m, 3H), 8.03 (d, J=8 Hz, 2H), 12.2 (br s, 1H); MS, m/z, 473 (M−H)−.

Workup

concentrationThe reaction was concentrated at RT
customdried under high vacuum

Sources & evidence

ORD record: ord-b9388c370fd94b6d9cc8f5423bcfb18d
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442833B2

Reaction notes

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