Lithium Hydroxide → HCID 68592856, compound

HRID 1429169Notes

Reaction equation

HRID 1429169 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[CH:32]=[C:31]([C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)[N:30]=[C:29]([O:41][CH3:42])[N:28]=3)[CH2:12]1)[C:8](=[O:43])[NH:7]2)=[O:5])C.[Li+].[OH-]>C1COCC1.CO>[CH3:42][O:41][C:29]1[N:28]=[C:27]([O:26][CH:11]2[CH2:10][CH:9]3[CH:13]([C:14](=[O:25])[N:15]([CH3:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][CH:22]4[C:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]3=[O:43])[CH2:23]4)[CH2:12]2)[CH:32]=[C:31]([C:33]2[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=2)[N:30]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68590782HCID 68590782, compound

Product 1

HCID 68592856HCID 68592856, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of the ethyl ester 16e (1.2 g, 2 mmol) in THF/MeOH 1:1 (30 ml) was treated with a 1M solution of LiOH as described in Example 13 step d. Purification by column chromatography on silica gel gave the crude title compound, (400 mg, 77%), (M+H)+565.

Workup

  1. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-fa22655053c2431eb22a5d43eb42462f
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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