Methanol → 4-({[2-[(tert-Butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)benzoic acid

HRID 1013494Notes

Reaction equation

HRID 1013494 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=1)=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.CO.[Li+].[OH-]>CCOC(C)=O.C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=1)=[O:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 57607810Methyl 4-[({2-[(tert-butoxycarbonyl)amino]-5-thien-2-ylphenyl}amino)carbonyl]benzoate

Product 1

HCID 579259154-({[2-[(tert-Butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-({[2-[(tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)benzoate (3.20 g, 7.07 mmol) in 1:1:2 H2O:MeOH:THF (80 mL) was added LiOH (1.20 g, 50.1 mmol). The reaction was stirred at room temperature for 18 h, diluted with EtOAc, washed with 2 N HCl, dried (Na2SO4), and evaporated to give the desired product as a red solid. MS: cal'd 461 (MNa+), exp 461 (MNa+).

Workup

  1. washwashed with 2 N HCl
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-27baf62019a04014b3aa999465614150
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

Loading…