Sodium Hydroxide → HCID 9915127, compound

HRID 393089Notes

Reaction equation

HRID 393089 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[O:26])[CH:22]=[C:21]([Cl:36])[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].[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[O:26])[CH:22]=[C:21]([Cl:36])[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

5

Reactant 2

HCID 14798Sodium HydroxideHCID 131723042HCID 131723042, compound

Product 1

HCID 9915127HCID 9915127, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-[(thiophene-2-carbonyl)amino]-L-alanine, methyl ester (2.41 g, 4.4 mmol) in methanol (100 mL) and sodium hydroxide (0.35 g, 8.8 mmol) in water (2 mL) was stirred at room temperature overnight and then the solvents were evaporated. The residue was partitioned between water and ethyl acetate and the ethyl acetate layer was discarded. The aqueous layer was acidified with 1 M HCl, and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, and the product started to precipitate. The solvents were evaporated from the organic layer, and dichloromethane/hexanes was added to the residue. The solid was filtered off, dried overnight under high vacuum, and taken up again in dichloromethane/hexanes. The solid was filtered off, and then dried overnight under high vacuum to give N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-[(thiophene-2-carbonyl)amino]-L-alanine (2.10 g, 89%) as a white solid.

Workup

  1. customthe solvents were evaporated
  2. customThe residue was partitioned between water and ethyl acetate
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. customto precipitate
  6. customThe solvents were evaporated from the organic layer, and dichloromethane/hexanes
  7. additionwas added to the residue
  8. filtrationThe solid was filtered off
  9. customdried overnight under high vacuum
  10. filtrationThe solid was filtered off
  11. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-60450f0355be41fbb175866a2bc95642
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

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