Lithium Hydroxide → HCID 178514388, compound

HRID 378122Notes

Reaction equation

HRID 378122 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]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:26][C:27]([O:29]CC)=[O:28])=[O:23])=[O:19])[CH:15]=[CH:16][CH:17]=1.[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]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:26][C:27]([OH:29])=[O:28])=[O:23])=[O:19])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 178472104HCID 178472104, compound

Product 1

HCID 178514388HCID 178514388, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the product of Example 3 (0.37 g, 0.0007 mole) in H2O (10 ml) was added LiOH (80 mg, 0.002 mole). The reaction mixture was stirred at room temperature for 1 hour. The pH was lowered to ≃3 with TFA and the product was isolated by RPHPLC to yield β-[[2-[[[3-[(aminoiminomethyl)amino]phenyl]carbonyl]-amino]acetyl]amino]benzenepropanoic acid, trifluoroacetate salt (280 mg) as a white solid. MS and NMR were consistent with the desired structure.

Workup

  1. customthe product was isolated by RPHPLC

Sources & evidence

ORD record
ord-ce0e0b8514654da0a45c7092e291cef0
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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