Trifluoroacetic acid → HCID 11429178, compound

HRID 1869267Notes

Reaction equation

C([O:5][C:6](=[O:28])[CH2:7][NH:8][S:9]([C:12]1[S:13][C:14]([CH2:17][NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[O:20])=[CH:15][CH:16]=1)(=[O:11])=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]([NH:18][CH2:17][C:14]2[S:13][C:12]([S:9]([NH:8][CH2:7][C:6]([OH:28])=[O:5])(=[O:10])=[O:11])=[CH:16][CH:15]=2)=[O:20])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1c (400 mg, 0.9 mmole) in CH2Cl2 (10 ml) at 0° C. is added TFA (10 ml) and the reaction is stirred for 1 h at 0° C. and a further hour at room temperature. Evaporating the solvents to dryness gave 1d (300 mg, 86%) as a white solid. 1H NMR (d6-DMSO) δ 9.34 (t, J=5.65 Hz, 1H), 8.20 (t, J=6.03 Hz, 1H), 7.89 (d, J=8.67 Hz, 2H), 7.56 (d, J=8.67 Hz, 2H), 7.43 (d, J=3.77 Hz, 1H), 7.05 (d, J=3.77 Hz, 1H), 4.63 (d, J=5.65 Hz, 2H), 3.59 (d, J=6.03 Hz, 2H).

Workup

customEvaporating the solvents to dryness

Sources & evidence

ORD record: ord-ea275aedb9c04a90915057f56c5995ab
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638538B1

Reaction notes

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