Hydrochloric Acid → (2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol

HRID 1024549Notes

Reaction equation

HRID 1024549 reaction equation
C([O:4][CH2:5][CH:6]([OH:23])[C@@H:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.C[O-].[Na+].CO.Cl>CO>[C:19]([O:18][C:16]([NH:15][C@@H:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C@H:6]([OH:23])[CH2:5][OH:4])=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23694274Sodium methanolate methanolHCID 68194104(3S)-3-([(1,1-dimethylethyl)oxy]carbonylamino)-2-hydroxy-4-phenylbutyl ethanoate

Product 1

HCID 10967943(2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a suitable reactor was added 4a (52.3 g, 162 mmol), MeOH (810 mL), and 25% NaOMe/MeOH (8.1 mmol) at 20-30° C. under N2. The mixture was stirred at 20-30° C. for 2 hr, and 1 N HCl aqueous solution (16.2 mmol) was added at this temperature. The separated organic portion was concentrated at 40-50° C. under reduced pressure. Toluene (1100 mL) was added and the mixture was heated to 108-110° C. for dissolution. The mixture was cooled to 45-50° C. and stirred for 30 min. The mixture was further cooled to 20-30° C. and stirred for 1 hr. The mixture was filtered, and the filtered cake was washed with toluene (220 mL). The wet cake was dried at 40-50° C. under reduced pressure to give diol 7 as an off-white to white powder (39.5 g, 87% yield).

Workup

  1. concentrationThe separated organic portion was concentrated at 40-50° C. under reduced pressure
  2. additionToluene (1100 mL) was added
  3. temperaturethe mixture was heated to 108-110° C. for dissolution
  4. temperatureThe mixture was cooled to 45-50° C.
  5. stirringstirred for 30 min
  6. temperatureThe mixture was further cooled to 20-30° C.
  7. stirringstirred for 1 hr
  8. filtrationThe mixture was filtered
  9. washthe filtered cake was washed with toluene (220 mL)
  10. customThe wet cake was dried at 40-50° C. under reduced pressure

Sources & evidence

ORD record
ord-1e03077983f040e987e6cf2cc9594636
Source dataset
uspto-grants-2014_05
Patent number
US08722921B2

Reaction notes

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