Lithium Hydroxide → HCID 68409047, compound

HRID 1443488Notes

Reaction equation

C([O:3][C:4]([C:6]12[CH2:23][CH:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:24])[C:14](=[O:25])[CH:13]1[CH:9]([CH2:10][CH:11]([O:26][C:27]3[C:36]4[C:31](=[C:32]([CH3:39])[C:33]([O:37][CH3:38])=[CH:34][CH:35]=4)[N:30]=[C:29]([C:40]4[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=4)[N:28]=3)[CH2:12]1)[C:8](=[O:48])[NH:7]2)=[O:5])C.BrCC(=O)C(C)C.[OH-].[Li+]>C1COCC1>[CH3:38][O:37][C:33]1[C:32]([CH3:39])=[C:31]2[C:36]([C:27]([O:26][CH:11]3[CH2:10][CH:9]4[CH:13]([C:14](=[O:25])[N:15]([CH3:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][CH:22]5[C:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]4=[O:48])[CH2:23]5)[CH2:12]3)=[N:28][C:29]([C:40]3[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=3)=[N:30]2)=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Compound 136 (420 mg, 0.639 mmol) was dissolved in a 96 mL solvent mixture (THF 2:methanol 1:water 1). Aqueous lithium hydroxide (6.4 mL, 1M) was added and the reaction mixture was heated at 50° C. over-night. Purification by column chromatography (silica gel, 5% methanol in dichloromethane) gave the title compound (230 mg, 57%). MS (M+H)+ 629.

Workup

customPurification by column chromatography (silica gel, 5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-a03e5df9b443497d8e320c6f34a00f24
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659245B2

Reaction notes

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