2,4-Dimethylbenzaldehyde → HCID 11295807, compound

HRID 1766840Notes

Reaction equation

HRID 1766840 reaction equation
C(O[C:9](=O)[NH:10][CH2:11][C@H:12]([NH:18][C:19](=[O:39])[CH2:20][C:21](=[O:38])[NH:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33](=[O:37])[N:34]([CH3:36])[CH3:35])[CH:24]=1)[C@@H:13]([OH:17])[C:14]#[C:15][CH3:16])C1C=CC=CC=1.[CH3:41][C:42]1[CH:49]=[C:48]([CH3:50])[CH:47]=[CH:46][C:43]=1C=O.C([BH3-])#N.[Na+]>CO.[Pd]>[CH3:41][C:42]1[CH:49]=[C:48]([CH3:50])[CH:47]=[CH:46][C:43]=1[CH2:9][NH:10][CH2:11][C@H:12]([NH:18][C:19](=[O:39])[CH2:20][C:21]([NH:22][C:23]1[CH:28]=[C:27]([C:29]([F:30])([F:32])[F:31])[CH:26]=[C:25]([C:33](=[O:37])[N:34]([CH3:35])[CH3:36])[CH:24]=1)=[O:38])[C@@H:13]([OH:17])[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 618142,4-DimethylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69287820HCID 69287820, compound

Product 1

HCID 11295807HCID 11295807, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of {(2S,3S)-2-[2-(3-dimethylcarbamoyl-5-trifluoromethyl-phenylcarbamoyl)-acetylamino]-3-hydroxy-hex-4-ynyl}-carbamic acid benzyl ester (186 mg, 0.33 mmol) in MeOH (6 mL) was charged with 5% Pd/C, Degussa style (37 mg), stirred under H2 (1 atm) for 12 h at RT, filtered, and concentrated in vacuo. The residue was dissolved in MeOH (6 mL). The resultant solution was charged sequentially with 2,4-dimethylbenzaldehyde (46 mg, 0.33 mmol) and sodium cyanoborohydride (25 mg, 0.4 mmol), stirred for 12 h at RT, quenched with sat. NaHCO3, and extracted twice with EtOAc. The organic extracts were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification of the residue by reverse-phase HPLC provided the title compound as a white powder after lyopholization. MS found: (M+H)+=551.3.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in MeOH (6 mL)
  4. stirringstirred for 12 h at RT
  5. customquenched with sat. NaHCO3
  6. extractionextracted twice with EtOAc
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification of the residue by reverse-phase HPLC

Sources & evidence

ORD record
ord-3509d7cbd649482d8dd38b93a391b3ee
Source dataset
uspto-grants-2007_06
Patent number
US07230133B2

Reaction notes

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