N,N-Diacetyl-O-methylhydroxylamine → HCID 58909414, compound

HRID 1985096Notes

Reaction equation

HRID 1985096 reaction equation
[NH2:1][C@@H:2]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[C:35]([F:40])[CH:34]=1)[C@H:3]([OH:31])[CH2:4][NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=2)[N:9]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:8][CH2:7]1.[C:41](N(C(=O)C)OC)(=[O:43])[CH3:42]>ClCCl>[C:41]([NH:1][C@@H:2]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[C:35]([F:40])[CH:34]=1)[C@H:3]([OH:31])[CH2:4][NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=2)[N:9]([C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:8][CH2:7]1)(=[O:43])[CH3:42]

Participants

4

Reactant 2

HCID 538412N,N-Diacetyl-O-methylhydroxylamineHCID 58909477HCID 58909477, compound

Product 1

HCID 58909414HCID 58909414, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 4-{[(2R,3S)-3-amino-4-(3,5-difluorophenyl)-2-hydroxybutyl]amino}-6-neopentyl-3,4-dihydroquinoline-1(2H)-carboxylate (0.226 g) in dichloromethane (5 mL) was added N,N-diacetyl-O-methylhydroxylamine (0.064 g). The mixture was stirred over the weekend at room temperature. The solvent was then removed under reduced pressure and the residue was partitioned between 1N HCl and ethyl acetate, dried with magnesium sulfate, filtered, and concentrated to give 0.243 g of the title compound. (99% yield). MS (ESI+) for C34H41F2N3O4 m/z 594.31 (M+H)+.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe residue was partitioned between 1N HCl and ethyl acetate
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a7cad6d4f4384e4197f6f6cb4b412b09
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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