Lithium hydroxide, monohydrate → HCID 53240754, compound

HRID 422175Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[CH:20]=[C:19]2[C:6]=1[C@@:7]1([CH3:31])[C@H:16]([CH2:17][S:18]2(=[O:27])=[O:26])[C@:15]2([CH3:28])[C@H:10]([C:11]([CH3:30])([CH3:29])[CH2:12][CH2:13][CH2:14]2)[CH2:9][CH2:8]1)=[O:4].O[Li].O>CO.O>[CH3:31][C@@:7]12[CH2:8][CH2:9][C@@H:10]3[C@:15]([CH3:28])([CH2:14][CH2:13][CH2:12][C:11]3([CH3:29])[CH3:30])[C@H:16]1[CH2:17][S:18](=[O:26])(=[O:27])[C:19]1[C:6]2=[C:5]([C:3]([OH:4])=[O:2])[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[CH:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (1R,10R,11S,16S)-3-(methoxycarbonyl)-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acid (84) (0.1 g, 0.2 mmol) and LiOH.H2O (0.1 g, 4 mmol) in MeOH (5.0 mL) and water (5.0 mL) was heated at 90° C. for 72 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure and acidified with 1 M HCl. The resulting solid was collected by filtration to give (1R,10R,11S,16S)-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo-[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3,5-dicarboxylic acid (85) (0.09 g, 94%) as a white solid. 1H NMR (CD3OD): δ 8.43 (d, 1H), 8.07 (d, 1H), 3.56 (m, 2H), 2.92 (d, 1H), 2.18 (d, 1H), 1.90-1.38 (m, 11H), 1.30-1.17 (m, 2H), 1.08-0.96 (m, 5H), 0.90 (s, 3H), 0.87 (s, 3H). MS m/z 433 (O23H30O6S−H+).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record: ord-39267900f3f14d168853dce46da11d02
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101605B2

Reaction notes

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