HCID 15481806, compound → (2R,3S)-3-(Formylhydroxyamino)-2-(3-phenyl-1-propyl)butanoic acid [(1S)-2,2-dimethyl-1-(methylcarbamoyl)-1-propyl]amide

HRID 565237Notes

Reaction equation

HRID 565237 reaction equation
[CH3:1][C:2]([CH3:34])([CH3:33])[C@H:3]([NH:8][C:9](=[O:32])[C@H:10]([CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:11]([N:13]([CH:21]=[O:22])[O:14]C1CCCCO1)[CH3:12])[C:4](=[O:7])[NH:5][CH3:6]>C(O)(=O)C.O>[CH3:33][C:2]([CH3:1])([CH3:34])[C@H:3]([NH:8][C:9](=[O:32])[C@H:10]([CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:11]([N:13]([CH:21]=[O:22])[OH:14])[CH3:12])[C:4](=[O:7])[NH:5][CH3:6]

Participants

3

Reactant 1

HCID 15481806HCID 15481806, compound

Product 1

HCID 9952396(2R,3S)-3-(Formylhydroxyamino)-2-(3-phenyl-1-propyl)butanoic acid [(1S)-2,2-dimethyl-1-(methylcarbamoyl)-1-propyl]amideYield 93%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A solution of (2R,3S)-3-(Formyl-2-tetrahydropyranyloxyamino)-2-(3-phenyl-1-propyl)butanoic acid [(1S)-2,2-dimethyl-1-(methylcarbamoyl)-1-propyl]amide (3.0 g, 6.32 mmol) in acetic acid-water (4:1, 10 mL) is heated to 50° C. for 16 h. The reaction mixture is concentrated, then dissolved in toluene and concentrated in vacuo. The procedure is repeated once again to afford the crude product which is triturated from hot dichloromethane-diethyl ether to provide (2R,3S)-3-(Formylhydroxyamino)-2-(3-phenyl-1-propyl)butanoic acid [(1S)-2,2-dimethyl-1-(methylcarbamoyl)-1-propyl]amide as a white solid (2.3 g, 93% yield).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. dissolutiondissolved in toluene
  3. concentrationconcentrated in vacuo
  4. customto afford the crude product which
  5. customis triturated from hot dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-b44cba5eb4d24861864f3592afd72cac
Source dataset
uspto-grants-2001_01
Patent number
US06172064B2

Reaction notes

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