Acetaldehyde → HCID 118061772, compound

HRID 632785Notes

Reaction equation

HRID 632785 reaction equation
[NH2:1][C@@H:2]1[CH2:6][N:5]([C:7]2[C:11]([NH:12][C:13]([C:15]3[N:16]=[C:17]([C:20]4[CH:25]=[CH:24][N:23]=[C:22]([N:26]([CH2:34][C:35]([F:38])([F:37])[F:36])C(=O)OC(C)(C)C)[CH:21]=4)[O:18][CH:19]=3)=[O:14])=[CH:10][N:9]([CH3:39])[N:8]=2)[C:4](=[O:40])[CH2:3]1.[CH:41](=O)[CH3:42].CO.[C:46](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:47].[Na+]>C1COCC1>[CH2:46]([N:1]([CH2:41][CH3:42])[C@@H:2]1[CH2:6][N:5]([C:7]2[C:11]([NH:12][C:13]([C:15]3[N:16]=[C:17]([C:20]4[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:34][C:35]([F:36])([F:37])[F:38])[CH:21]=4)[O:18][CH:19]=3)=[O:14])=[CH:10][N:9]([CH3:39])[N:8]=2)[C:4](=[O:40])[CH2:3]1)[CH3:47]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 131735451HCID 131735451, compound

Product 1

HCID 118061772HCID 118061772, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (4-(4-((3-((4S)-4-amino-2-oxopyrrolidin-1-yl)-1-methyl-1H-pyrazol-4-yl)carbamoyl)-1,3-oxazol-2-yl)pyridin-2-yl)(2,2,2-trifluoroethyl)carbamate (82 mg) and acetaldehyde (32 mg) in THF (0.24 mL)/methanol (0.48 mL) was added sodium triacetoxyborohydride (154 mg), and the mixture was stirred at 0° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in TFA (0.70 mL), and the solution was stirred at room temperature for 20 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate), and recrystallized from ethyl acetate/hexane to give the title compound (34 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in TFA (0.70 mL)
  3. stirringthe solution was stirred at room temperature for 20 min
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)
  6. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f6e8cc00439d4d76b7e94b7c48d8d188
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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