Potassium Hydroxide → 2-[4-({[2-[(Tert-butoxycarbonyl)amino]-5-(3-thienyl)phenyl]amino}carbonyl)-phenyl]-3-{[(methylamino)carbonyl]amino}propanoic acid

HRID 1919911Notes

Reaction equation

HRID 1919911 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([CH:29]([CH2:34][NH:35][C:36]([NH:38][CH3:39])=[O:37])[C:30]([O:32]C)=[O:31])=[CH:25][CH:24]=1)=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C1COCC1.CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:24]=[CH:25][C:26]([CH:29]([CH2:34][NH:35][C:36]([NH:38][CH3:39])=[O:37])[C:30]([OH:32])=[O:31])=[CH:27][CH:28]=1)=[O:22])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 57611887Methyl 2-[4-({[2-[(tert-butoxycarbonyl)amino]-5-(3-thienyl)phenyl]amino}carbonyl)phenyl]-3-{[(methylamino)carbonyl]-amino}propanoate

Product 1

HCID 576119482-[4-({[2-[(Tert-butoxycarbonyl)amino]-5-(3-thienyl)phenyl]amino}carbonyl)-phenyl]-3-{[(methylamino)carbonyl]amino}propanoic acid

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-[4-({[2-[(tert-butoxycarbonyl)amino]-5-(3-thienyl)phenyl]amino}carbonyl)phenyl]-3-{[(methylamino)carbonyl]-amino}propanoate (420 mg, 0.76 mmol) in THF (4 mL) and MeOH (1.5 mL) was added KOH (1N, 0.91 mL, 0.91 mmol). After stirring at room temperature for 1 h, the mixture was diluted with 1 M citric acid and extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), and concentrated to yield 2-[4-({[2-[(tert-butoxycarbonyl)amino]-5-(3-thienyl)phenyl]amino}carbonyl)-phenyl]-3-{[(methylamino)carbonyl]amino}propanoic acid as an off-white powder. MS (ESI) calcd [M+H]+ 539.2, found 539.1.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-335cb8e6df3c4ca785014b0c39b9d46c
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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