Water → HCID 59977300, compound

HRID 1726790Notes

Reaction equation

HRID 1726790 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[C:33]([OH:35])[CH:32]=[C:31]([OH:36])[CH:30]=2)=[O:26])[CH:22]=[CH:21][C:3]=1[C:4]([NH:6][C@H:7]([C:17]([O:19]C)=[O:18])[CH2:8][NH:9][C:10]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)=[O:11])=[O:5].O.[OH-].[Li+].O>O1CCCC1.CO>[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[C:33]([OH:35])[CH:32]=[C:31]([OH:36])[CH:30]=2)=[O:26])[CH:22]=[CH:21][C:3]=1[C:4]([NH:6][C@H:7]([C:17]([OH:19])=[O:18])[CH2:8][NH:9][C:10]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)=[O:11])=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 131723038HCID 131723038, compound

Product 1

HCID 59977300HCID 59977300, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[2-chloro-4-[[[(3,5-dihydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-[thiophene-2-carbonyl]amino-L-alanine, methyl ester (250 mg, 0.47 mmol), and lithium hydroxide monohydrate (200 mg, 4.8 mmol) in tetrahydrofuran (30 mL), methanol (10 mL), and water (10 mL) was stirred at room temperature overnight. The solution was concentrated to remove methanol and tetrahydrofuran, and then water (50 mL) and 1 M HCl (20 mL) were added. The mixture was extracted with ethyl acetate (2×30 mL), and the solvent was evaporated from the extracts. The residue was dissolved in methanol (30 mL) and 10 mL of this solution was purified by HPLC to give N-[2-chloro-4-[[[(3,5-dihydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-[thiophene-2-carbonyl]amino-L-alanine (21.2 mg, 26%) as an off-white solid.

Workup

  1. concentrationThe solution was concentrated
  2. customto remove methanol and tetrahydrofuran
  3. additionwater (50 mL) and 1 M HCl (20 mL) were added
  4. extractionThe mixture was extracted with ethyl acetate (2×30 mL)
  5. customthe solvent was evaporated from the extracts
  6. dissolutionThe residue was dissolved in methanol (30 mL)
  7. custom10 mL of this solution was purified by HPLC

Sources & evidence

ORD record
ord-536262c3770e48e1bcb13f8e4062dca6
Source dataset
uspto-grants-2009_02
Patent number
US07491741B2

Reaction notes

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