Lithium Hydroxide → HCID 178514394, compound

HRID 378127Notes

Reaction equation

HRID 378127 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:22]([NH:24][CH2:25][C:26]([NH:28][CH:29]([C:36]2[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[C:38]([C:46]([F:49])([F:48])[F:47])[CH:37]=2)[CH2:30][C:31]([O:33]CC)=[O:32])=[O:27])=[O:23])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[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:22]([NH:24][CH2:25][C:26]([NH:28][CH:29]([C:36]2[CH:37]=[C:38]([C:46]([F:47])([F:48])[F:49])[CH:39]=[C:40]([C:42]([F:43])([F:44])[F:45])[CH:41]=2)[CH2:30][C:31]([OH:33])=[O:32])=[O:27])=[O:23])[CH:15]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:17]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 178472109HCID 178472109, compound

Product 1

HCID 178514394HCID 178514394, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 600 mg (0.00082 mole) of the product of Example 38 in 12 ml of H2O and 12 ml of CH3CN was added 140 mg (0.0033 mole) of LiOH. The reaction was stirred at room temperature for 1.5 hours. The pH was lowered to 2.5 with TFA and the product isolated by reverse phase prep HPLC to yield (after lyophilization) 520 mg of (±) β-[[2-[[[3-[(aminoiminomethyl)amino]-5-(trifluoromethyl)phenyl]carbonyl]amino]acetyl]amino]-3,5-bis(trifluoromethyl)benzenepropanoic acid, trifluoroacetate salt as a white solid.

Workup

  1. customthe product isolated by reverse phase prep HPLC

Sources & evidence

ORD record
ord-f6620de53d6b4416bf4894a5f7d5a6a0
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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