Methanol → HCID 15916893, compound

HRID 462899Notes

Reaction equation

HRID 462899 reaction equation
CO.C(OC([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][C@H:18]([OH:23])[CH2:19][C:20]([NH2:22])=[O:21])=O)C1C=CC=CC=1>[C].[Pd].C(O)(=O)C>[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C@H:18]([OH:23])[CH2:19][C:20]([NH2:22])=[O:21]

Participants

5

Reactant 2

HCID 887MethanolHCID 15916891HCID 15916891, compound

Product 1

HCID 15916893HCID 15916893, compoundYield 105.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

Into a mixture of 10 ml of 90% aqueous methanol and 0.01 ml of acetic acid was dissolved 350 mg (1.19 mmoles) of (S)-7-benzyloxycarbonylamino-3-hydroxyheptanamide. After adding 50 mg of 5% palladium-carbon, the mixture was stirred under a hydrogen stream at room temperature for 3 hours. After removal of the catalyst by filtration, the filtrate was evaporated to dryness, dissolved again in a small volume of water and passed through a column (12 mm inner diameter) containing 30 ml of Dowex® 50W-X4 (H-type). The column was washed with 90 ml of water and eluted with 0.5M aqueous ammonia (3 ml in fraction size). The fraction Nos. 28 to 34 were combined and evaporated to dryness to yield 201 mg (96% yield) of (S)-7-amino-3-hydroxyheptanamide; [α]D22 -2° (c 2, water).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe filtrate was evaporated to dryness
  4. dissolutiondissolved again in a small volume of water
  5. additioncontaining 30 ml of Dowex®
  6. washThe column was washed with 90 ml of water
  7. washeluted with 0.5M aqueous ammonia (3 ml in fraction size)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-256c2114e0e340cc8c371d772002fa17
Source dataset
uspto-grants-1985_05
Patent number
US04518532

Reaction notes

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