Sodium Hydroxide → HCID 57320946, compound

HRID 496628Notes

Reaction equation

HRID 496628 reaction equation
[CH2:1]([C:8]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:9]=1[C:10]([NH:12][C@@H:13]([CH2:18][CH2:19][S:20][CH3:21])[C:14]([O:16]C)=[O:15])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([C:8]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:9]=1[C:10]([NH:12][C@@H:13]([CH2:18][CH2:19][S:20][CH3:21])[C:14]([OH:16])=[O:15])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57210671HCID 57210671, compound

Product 1

HCID 57320946HCID 57320946, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (2S)-2-(2-benzyl-5-nitro-benzoylamino)-4-methylsulfanyl-butyrate compound 34(d) (25.24 g, 62.78 mmol) in methanol (500 mL) was treated with 2N aqueous sodium hydroxide solution (35 mL, 70 mmol). The resulting solution was then evaporated to dryness and the solids partitioned between ethyl ether (200 mL) and water (500 mL). The aqueous material was then acidified to pH2 with 2N HCl and extracted with ethyl acetate (2×250 mL). The combined organics were washed with water(2×100 mL), brine(100 mL), filtered through phase separating paper and evaporated to give (2S)-2-(2-benzyl-5-nitro-benzoylamino)-4-methylsulfanyl-butyric acid (compound 36(a)) as a white solid, 23.57 g(96.8%).

Workup

  1. customThe resulting solution was then evaporated to dryness
  2. customthe solids partitioned between ethyl ether (200 mL) and water (500 mL)
  3. extractionextracted with ethyl acetate (2×250 mL)
  4. washThe combined organics were washed with water(2×100 mL), brine(100 mL)
  5. filtrationfiltered through phase
  6. customseparating paper
  7. customevaporated

Sources & evidence

ORD record
ord-01c957580196442484f4d2b280f6457d
Source dataset
uspto-grants-2005_09
Patent number
US06946468B1

Reaction notes

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