Potassium Hydroxide → HCID 57616341, compound

HRID 2042942Notes

Reaction equation

S([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C@H:20]2[C@H:25]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@@H:24]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@H:23]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C@@H:22]([CH2:50][O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[O:21]2)=[CH:12]1)(C1C=CC(C)=CC=1)(=O)=O.[OH-].[K+]>CCO.C1COCC1>[CH2:27]([O:26][C@@H:25]1[C@@H:24]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C@H:23]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C@@H:22]([CH2:50][O:51][CH2:52][C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)[O:21][C@H:20]1[C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:11][CH:12]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of compound 84 (740 mg, 0.93 mmol) in a mixture of EtOH (20 mL) and THF (10 ml) was added KOH (250 mg). The reaction mixture was stirred at 50° C. for 1 d. After reaction complete, the resulting solution was quenched with 1.0 M HCl and organic layer was extracted with EtOAc. After evaporating volatile material under reduced pressure, the residue was purified with normal phase column chromatography to afford titled compound 85 (370 mg, 62%) as off-white solid.

Workup

customAfter reaction complete
customthe resulting solution was quenched with 1.0 M HCl and organic layer
extractionwas extracted with EtOAc
customAfter evaporating volatile material under reduced pressure
customthe residue was purified with normal phase column chromatography

Sources & evidence

ORD record: ord-c874821faf3f42e5a9622cbc530836c3
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586550B2

Reaction notes

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