Lithium Hydroxide → HCID 178427456, compound

HRID 378138Notes

Reaction equation

HRID 378138 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][N:9]=[CH:10][NH:11][C:12]1[CH:13]=[C:14]([C:18]([NH:20][CH2:21][C:22]([NH:24][CH:25]([CH2:31][NH:32][S:33]([C:36]2[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH2:26][C:27]([O:29]C)=[O:28])=[O:23])=[O:19])[CH:15]=[CH:16][CH:17]=1.CC#N.[Li+].[OH-].C(O)(C(F)(F)F)=O>O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][N:9]=[CH:10][NH:11][C:12]1[CH:13]=[C:14]([C:18]([NH:20][CH2:21][C:22]([NH:24][CH:25]([CH2:31][NH:32][S:33]([C:36]2[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH2:26][C:27]([OH:29])=[O:28])=[O:23])=[O:19])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 178500538HCID 178500538, compound

Product 1

HCID 178427456HCID 178427456, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the product of Example 64 (180 mg) in 1:1 CH3CN:H2O (4 ml) was treated with LiOH (100 mg). After 2 hours, the reaction was acidified with TFA and purified by HPLC (RP--CH3CN/H2O). The title compound (100 mg) was isolated as a white solid. MS, 1H-NMR and CHN analysis were consistent with the desired product.

Workup

  1. custompurified by HPLC (RP--CH3CN/H2O)

Sources & evidence

ORD record
ord-b1a9dfc661e149988dc0d9db32565926
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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