Acetaldehyde → HCID 118061332, compound

HRID 632787Notes

Reaction equation

HRID 632787 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].[BH4-].[Na+].CO>C1COCC1>[CH2:41]([NH: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]([NH:26][CH2:34][C:35]([F:37])([F:36])[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)[CH3:42]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 887MethanolHCID 4311764Sodium borohydrideHCID 131735451HCID 131735451, compound

Product 1

HCID 118061332HCID 118061332, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 (42 mg) in THF (1.0 mL) was added acetaldehyde (37 μL), and the mixture was stirred overnight at room temperature. Sodium borohydride (28 mg) and methanol (0.20 mL) were added thereto, and the mixture was stirred at room temperature for 1 hr, and 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 (14 mg).

Workup

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

Sources & evidence

ORD record
ord-212e3e42f2d14863aeda2b699d415e7e
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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