Hydrochloric Acid → HCID 66615893, compound

HRID 76037Notes

Reaction equation

HRID 76037 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[O:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]4[CH2:27][CH2:26][CH:25](CC=O)[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1.[OH2:31].Cl>C1COCC1>[CH2:19]([O:31][C:13](=[O:12])/[CH:16]=[CH:17]/[CH2:18][CH:25]1[CH2:26][CH2:27][CH:22]([C:19]2[CH:18]=[CH:17][C:16]([C:13]3[O:12][C:11]([NH:10][C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=4)=[N:15][CH:14]=3)=[CH:21][CH:20]=2)[CH2:23][CH2:24]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24758Sodium hydrideHCID 86634689HCID 86634689, compound

Product 1

HCID 66615893HCID 66615893, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of (benzyloxycarbonylmethyl)-triphenylphosphionium bromide (315 mg, 0.642 mmol) in THF (6 mL) at 0° C. is added NaH (60% in mineral oil, 27 mg, 0.642 mmol) and the suspension is allowed to stir at 0° C. for 30 min. (4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetaldehyde (253 mg, 0.642 mmol) in THF (4 mL) is added dropwise. The reaction mixture is then stirred a 0° C. for 30 min and the at ambient temperature for 18 h. Water (10 mL) and HCl solution (1N, 15 mL) is added, and the reaction mixture is extracted with EtOAc (3×15 mL). The organic phase is washed with water (1×5 mL), brine (3×20 mL), dried and concentrated to give the title compound (279 mg) as an off-white solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.02-1.14 (m, 2H) 1.34-1.49 (m, 3H) 1.59-1.73 (m, 1H) 1.80-1.87 (m, 3H) 2.11 (t, J=8.00 Hz, 2H) 2.46 (ddd, J=11.68, 9.16, 2.91 Hz, 1H) 5.11 (s, 2H) 5.82 (d, J=15.66 Hz, 1H) 6.90-6.99 (m, 1H) 7.14-7.17 (d, 8.08 Hz, 2H) 7.24-7.28 (m, 3H) 7.28-7.32 (m, 6H) 7.40 (d, J=8.08 Hz, 1H) 7.49 (s, 1H); (M+H)+527.2.

Workup

  1. additionis added dropwise
  2. waitthe at ambient temperature for 18 h
  3. extractionthe reaction mixture is extracted with EtOAc (3×15 mL)
  4. washThe organic phase is washed with water (1×5 mL), brine (3×20 mL)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aa4d27670a184f188bbecb15c4b22f73
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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