Methanol → HCID 15916893, compound

HRID 1388173Notes

Reaction equation

HRID 1388173 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 addition of 50 mg of 5% palladium-carbon, the mixture was stirred under a hydrogen stream for 3 hours at room temperature. After removal of the catalyst by filtration, the filtrate was evaporated to dryness, then dissolved again in a small volume of water, and passed through a column (12 mm in inner diameter) packed with 30 ml of Dowex® 50 W-X4 (H-type). The column was then washed with 90 ml of water and eluted with 0.5 M aqueous ammonia. Fraction Nos. 28 to 34 (each 3 ml in volume) were combined and evaporated to dryness to obtain 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. washThe column was then washed with 90 ml of water
  6. washeluted with 0.5 M aqueous ammonia
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-e13166c4caa24474b5e33cf8a0fff829
Source dataset
uspto-grants-1984_02
Patent number
US04430346

Reaction notes

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