Lithium Hydroxide → 18-(tert-Butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid

HRID 1445424Notes

Reaction equation

HRID 1445424 reaction equation
C([O:3][C:4]([C:6]12[CH2:24][CH:23]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C:14](=[O:34])[N:13]1[CH:9]([CH2:10][CH:11]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:12]1)[C:8](=[O:43])[NH:7]2)=[O:5])C.[Li+].[OH-]>C1COCC1.CO.O>[C:39]([Si:36]([CH3:38])([CH3:37])[O:35][CH:11]1[CH2:10][CH:9]2[N:13]([C:14](=[O:34])[N:15]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH:23]3[C:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]2=[O:43])[CH2:24]3)[CH2:12]1)([CH3:42])([CH3:41])[CH3:40]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 6687134618-(tert-Butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl ester

Product 1

HCID 6867769918-(tert-Butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acidYield 75%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Compound 126 (450 mg, 0.734 mmol) was dissolved in THF/MeOH/H2O (2:1:1). LiOH, 1M (7.4 ml, 7.4 mmol) was added and the reaction mixture was allowed to stir at RT over night. Acidification (5% citric acid) followed by extraction with chloroform gave the title compound (321 mg, 75%). M+H=586.

Workup

  1. extractionAcidification (5% citric acid) followed by extraction with chloroform

Sources & evidence

ORD record
ord-88baba3737e04711b9e71d1acbef9599
Source dataset
uspto-grants-2010_02
Patent number
US07666834B2

Reaction notes

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