Ethanol → HCID 178445786, compound

HRID 713955Notes

Reaction equation

HRID 713955 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5].[C:8]([C@H:12]1[CH2:17][CH2:16][C@H:15]([O:18][C:19]2[C:20]([C:31]([F:34])([F:33])[F:32])=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH:25]=[C:24]([CH:29]=O)[CH:23]=[CH:22]3)[CH2:14][CH2:13]1)([CH3:11])([CH3:10])[CH3:9].C(O)C.C([BH3-])#N.[Na+]>>[C:8]([C@H:12]1[CH2:17][CH2:16][C@H:15]([O:18][C:19]2[C:20]([C:31]([F:32])([F:33])[F:34])=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH:25]=[C:24]([CH2:29][NH:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5])[CH:23]=[CH:22]3)[CH2:14][CH2:13]1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 4

HCID 702EthanolHCID 1123TaurineHCID 5003444Sodium cyanoborohydrideHCID 178445788HCID 178445788, compound

Product 1

HCID 178445786HCID 178445786, compound

Procedure

Taurine (0.03737 g, 0.2986 mmol) was added to a solution of 6-(trans-4-tert-butylcyclohexyloxy)-5-(trifluoromethyl)-2-naphthaldehyde (0.1130 g, 0.2986 mmol) in Ethanol (3.00 mL, 51.4 mmol) and the mixture was refluxed for 1 hour. The mixture was cooled to room temperature and Sodium cyanoborohydride (0.02252 g, 0.3583 mmol) was added. The mixture was then refluxed overnight. The reaction mixture was cooled to room temperature, washed with saturated aqueous citric acid solution (4 ml), then concentrated to dryness under reduced pressure. The resulting solid was washed with water and filtered. The residue was washed with water (10 mL), ether (10 mL) and hexane (10 mL) consecutively, then filtered. The residue was purified by prep HPLC to give the title compound. ESI-MS(M+H+): 488.3; 1H NMR (400 MHz, DMSO-d6) Shift 8.46-8.52 (m, 1H), 7.83-7.88 (m, 1H), 7.73-7.80 (m, 2H), 7.35-7.40 (m, 2H), 4.21-4.30 (m, 1H), 4.02 (br. s., 2H), 2.88 (t, J=6.78 Hz, 2H), 2.50 (d, J=13.80 Hz, 2H), 1.77-1.85 (m, 2H), 1.43-1.52 (m, 2H), 1.00-1.13 (m, 2H), 0.67-0.92 (m, 3H), 0.53 (s, 9H).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureThe mixture was then refluxed overnight
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washwashed with saturated aqueous citric acid solution (4 ml)
  5. concentrationconcentrated to dryness under reduced pressure
  6. washThe resulting solid was washed with water
  7. filtrationfiltered
  8. washThe residue was washed with water (10 mL), ether (10 mL) and hexane (10 mL) consecutively
  9. filtrationfiltered
  10. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-fe5da49d6df04b2e985da7747f41425f
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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