Hydrochloric Acid → (2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)-amide

HRID 1612428Notes

Reaction equation

HRID 1612428 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:12])(C)(C)C.Cl>O1CCOCC1>[CH3:19][C:17]([CH3:18])([CH3:20])[CH2:16][CH2:15][NH:14][C:13](=[O:21])[C@H:11]([CH3:12])[CH2:10][C@H:9]([OH:22])[C@@H:8]([NH2:7])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69507916[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-carbamic acid t-butyl ester

Product 1

HCID 68890142(2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)-amideYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-carbamic acid t-butyl ester (D1) (264 mg, 0.63 mmol) was treated with 4M HCl in dioxane (5 ml) and the resulting solution was stirred at room temperature for 1 h. It was then evaporated to dryness and the residue was partitioned between satd. aq. sodium carbonate and ethyl acetate. The aqueous layer was separated and extracted with further ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated to afford product (179 mg, 89%).

Workup

  1. customIt was then evaporated to dryness
  2. customthe residue was partitioned between satd
  3. customThe aqueous layer was separated
  4. extractionextracted with further ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ed53054bab33447c8516de23ebd44c47
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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