Nitrogen → HCID 57336781, compound

HRID 527250Notes

Reaction equation

HRID 527250 reaction equation
N#N.C([O:9][C:10]1([C:13]2[N:14]=[C:15]([CH2:18][N:19]3[N:23]=[C:22]([NH:24][C:25]([C:27]4[N:28]=[C:29]([CH3:39])[O:30][C:31]=4[C:32]4[CH:33]=[C:34]([CH3:38])[CH:35]=[CH:36][CH:37]=4)=[O:26])[CH:21]=[N:20]3)[O:16][CH:17]=2)[CH2:12][CH2:11]1)(=O)C(C)(C)C.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[OH:9][C:10]1([C:13]2[N:14]=[C:15]([CH2:18][N:19]3[N:23]=[C:22]([NH:24][C:25]([C:27]4[N:28]=[C:29]([CH3:39])[O:30][C:31]=4[C:32]4[CH:33]=[C:34]([CH3:38])[CH:35]=[CH:36][CH:37]=4)=[O:26])[CH:21]=[N:20]3)[O:16][CH:17]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 67958869HCID 67958869, compound

Product 1

HCID 57336781HCID 57336781, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(2-((4-(2-methyl-5-(m-tolyl)oxazole-4-carboxamido)-2H-1,2,3-triazol-2-yl)methyl)oxazol-4-yl)cyclopropyl pivalate (70 mg, 0.14 mmol) in THF (1.4 mL) was treated at 0° C. with DiBAL-H (0.7 mL of a 1M solution in THF, 0.70 mmol) and the resulting solution was stirred for 3.5 h at 0° C. The reaction mixture was poured onto a Rochelle's salt aq. solution (14 mL) and the mixture was vigorously stirred for 2 h at rt. The two layers were separated and the aq. phase was extracted with EA (14 mL). The combined org. layers were dried over MgSO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (4:6 hept-EA) gave the title compound as a yellow oil: TLC: rf (4:6 hept-EA)=0.30. LC-MS-conditions 06: tR=0.86 min, [M+H]+=421.22

Workup

  1. stirringthe mixture was vigorously stirred for 2 h at rt
  2. customThe two layers were separated
  3. extractionthe aq. phase was extracted with EA (14 mL)
  4. dry with materiallayers were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (4:6 hept-EA)

Sources & evidence

ORD record
ord-54e045006d69443da5266713a864e4c0
Source dataset
uspto-grants-2016_05
Patent number
US09346793B2

Reaction notes

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