Lithium Hydroxide → HCID 178514384, compound

HRID 378123Notes

Reaction equation

HRID 378123 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:40]=[CH:39][C:35]3[O:36][CH2:37][O:38][C:34]=3[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.CC#N>[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:40]=[CH:39][C:35]3[O:36][CH2:37][O:38][C:34]=3[CH:33]=2)[CH2:26][C:27]([OH:29])=[O:28])=[O:23])=[O:19])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 178472100HCID 178472100, compound

Product 1

HCID 178514384HCID 178514384, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To the product of Example 5 (0.35 g, 0.0006 mole) in H2O (40 ml) and CH3CN (5 ml) was added LiOH (70 mg, 0.0017 mole). The reaction mixture was stirred at room temperature for 1 hour. The pH was lowered to ≃4.5 with TFA and the product was isolated by RPHPLC to yield (±)β-[[2-[[[3-[(aminoiminomethyl)-amino]phenyl]carbonyl]amino]acetyl]amino]-1,3-benzodioxole-5-propanoic 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-6f604660d51842229b4a4aca3ca721ab
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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