Acetic Acid → (3R)-N-(benzyloxy)-6-cyclohexyl-3-{4-[(isopropylamino)methyl]-1,3-oxazol-2-yl}hexanamide

HRID 1350260Notes

Reaction equation

HRID 1350260 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:29])[CH2:11][C@H:12]([C:22]1OC=C(C=O)[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30]([NH2:33])([CH3:32])[CH3:31].[CH3:34][C:35]([OH:37])=O.[CH2:38](Cl)Cl>>[CH2:1]([O:8][NH:9][C:10](=[O:29])[CH2:11][C@H:12]([C:22]1[O:37][CH:35]=[C:34]([CH2:38][NH:33][CH:30]([CH3:32])[CH3:31])[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6344Dichloromethane2×HCID 6363IsopropylamineHCID 60077589(3R)-N-(benzyloxy)-6-cyclohexyl-3-(4-formyl-1,3-oxazol-2-yl)hexanamide

Product 1

HCID 21305024(3R)-N-(benzyloxy)-6-cyclohexyl-3-{4-[(isopropylamino)methyl]-1,3-oxazol-2-yl}hexanamideYield 32%

Procedure

A solution of (3R)-N-(benzyloxy)-6-cyclohexyl-3-(4-formyl-1,3-oxazol-2-yl)hexanamide (preparation 156) (200 mg, 0.50 mmol) in DCM (10 ml) was treated with isopropylamine (43 μl, 0.50 mmol) and stirred at room temperature for 15 minutes. NaHB(OAc)3 (170 mg, 0.80 mmol) and AcOH (29 μl, 0.50 mmol) were added and the reaction mixture stirred at room temperature for 1 hour. The reaction mixture was diluted with DCM and washed with sat. NaHCO3 solution followed by brine. The organic extract was dried over anhydrous MgSO4 and filtered. The solvent was removed under reduced pressure. The crude material was purified on a silica column eluting with a solvent gradient of DCM:MeOH:NH3 (100:0:0) gradually changing to (95:5:0.5) to afford the title compound as a colourless oil (75 mg, 32%).

Workup

  1. stirringthe reaction mixture stirred at room temperature for 1 hour
  2. washwashed with sat. NaHCO3 solution
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customThe crude material was purified on a silica column
  8. washeluting with a solvent gradient of DCM:MeOH:NH3 (100:0:0)

Sources & evidence

ORD record
ord-4b8819e7fb6048cba3a5013cb921557d
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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