Lithium Hydroxide → HCID 9958820, compound

HRID 1829999Notes

Reaction equation

HRID 1829999 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:42])[CH:20]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:21][C:22]([NH:24][C:25]2[CH:35]=[CH:34][C:28]([C:29]([O:31]CC)=[O:30])=[CH:27][CH:26]=2)=[O:23])=[CH:14][CH:13]=1)=[O:10].C1COCC1.[Li+].[OH-]>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:42])[CH:20]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:21][C:22]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:34][CH:35]=2)=[O:23])=[CH:16][CH:17]=1)=[O:10]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 10120494HCID 10120494, compound

Product 1

HCID 9958820HCID 9958820, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 4-[(4-{[4-({[(2-methylphenyl)amino]carbonyl}amino)phenyl]amino}-4-oxo-3-phenylbutanoyl)amino]benzoate (160 mg, 0.28 mmol) was dissolved in water:THF (10 mL; 1:1; v:v) and LiOH (27 mg, 1.13 mmol) was added at 0° C. and the reaction mixture was stirred at r.t. for 24 h. The reaction mixture was acidified, the product was isolated by filtration and purified by flash chromatography (CH2Cl2/MeOH/AcOH; 10/1/0.5) (11 mg, 0.02 mmol). M.p. 169° C. TLC (DCM/MeOH 9/1) Rf 0.27, ESI-MS: 537[M+H]+.

Workup

  1. customthe product was isolated by filtration
  2. custompurified by flash chromatography (CH2Cl2/MeOH/AcOH; 10/1/0.5) (11 mg, 0.02 mmol)

Sources & evidence

ORD record
ord-9b1e2fae946d4d08b05bfcb234e0625a
Source dataset
uspto-grants-2006_06
Patent number
US07064229B2

Reaction notes

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