Water → HCID 58065502, compound

HRID 1964510Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][CH2:9][C@H:10]([CH3:44])[O:11][C:12]1[CH:13]=[C:14]([C:29]2[NH:33][C:32]([C:34]3[S:35][C:36]([C:39](OCC)=[O:40])=[CH:37][N:38]=3)=[CH:31][CH:30]=2)[CH:15]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH:17]=1.O.[OH-].[Na+]>O1CCCC1>[CH3:7][O:8][CH2:9][C@H:10]([CH3:44])[O:11][C:12]1[CH:13]=[C:14]([C:29]2[NH:33][C:32]([C:34]3[S:35][C:36]([CH2:39][OH:40])=[CH:37][N:38]=3)=[CH:31][CH:30]=2)[CH:15]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminum hydride (22 mg, 0.580 mmol) was suspended in tetrahydrofuran (2 mL). Ethyl 2-(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-1,3-thiazole-5-carboxylate (106 mg, 0.190 mmol) synthesized in Example (5c) was dissolved in tetrahydrofuran (2 mL), followed by dropwise addition at 0° C. under nitrogen atmosphere. After stirring at 0° C. for 30 minutes, water (22 μL) and an aqueous sodium hydroxide solution (5M, 88 μL) were added dropwise sequentially and slowly. After filtration through Celite, the solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-100%) to afford the desired compound (48 mg, yield 49%) as a pale yellow solid.

Workup

additionfollowed by dropwise addition at 0° C. under nitrogen atmosphere
filtrationAfter filtration through Celite
distillationthe solvent was distilled off under reduced pressure
customthe resulting residue was purified
washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-100%)

Sources & evidence

ORD record: ord-3d8676ab54524ee88218c33985a897de
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415359B2

Reaction notes

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