Trifluoroacetic acid → HCID 53875398, compound

HRID 1107170Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C@H:12]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@H:13]([CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:14]([O:16]C(C)(C)C)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([C@H:12]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C@H:13]([CH2:21][CH2:22][O:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:14]([OH:16])=[O:15])(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(±)-t-Butyl (2R*,3R*)-3-(4-methoxybenzenesulfonyl)-7-phenyl-2-(2-phenoxyethyl)heptanoate (0.3 g, 0.54 mmol) is dissolved in CH2Cl2 (7 mL), cooled to 0° C. and TFA (1 mL) is added slowly. The bath is removed and the reaction is stirred for 4 hours. The reaction is concentrated in vacuo and the residue purified by reverse phase HPLC (50-100% CH3CN in 0.1% TFA/H2O) to yield (±)-(2R*,3R*)-3-(4-methoxybenzenesulfonyl)-7-phenyl-2-(2-phenoxyethyl)heptanoic acid (0.19 g, 70%). 1H NMR (300 MHz, CDCl3) δ 7.81 (d, J=8.8 Hz, 2H), 7.29-7.15 (m, 5H), 7.08 (d, J=7.3 Hz, 2H), 6.98-6.91 (m, 3H), 6.81 (d, J=8.3 Hz, 2H), 4.17-4.03 (m, 2H), 3.83 (s, 3H), 3.80-3.75 (m, 1H), 3.17-3.14 (m, 1H), 2.58-2.50 (m, 3H), 2.30-2.18 (m, 1H), 1.90-1.77 (m, 2H), 1.60-1.45 (m, 3H), 1.41-1.30 (m, 1H); MS (FAB) m/e 497 (M+H)+.

Workup

customThe bath is removed
concentrationThe reaction is concentrated in vacuo
customthe residue purified by reverse phase HPLC (50-100% CH3CN in 0.1% TFA/H2O)

Sources & evidence

ORD record: ord-7e31f41a9a744132a8953baceb719b2b
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057369

Reaction notes

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