Hydrochloric Acid → (2S,3S)-3-(dibenzylamino)-2-hydroxyhexanoic acid

HRID 1972328Notes

Reaction equation

HRID 1972328 reaction equation
[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:9]([CH2:14][CH2:15][CH3:16])[C@H](O)C#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-:25].[Na+].[C:27]([O:30]CC)(=[O:29])[CH3:28].CCCCCC>>[CH2:17]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]([CH2:14][CH2:15][CH3:16])[C@H:28]([OH:25])[C:27]([OH:30])=[O:29])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexaneHCID 44223342(2S,3S)-3-(dibenzylamino)-2-hydroxyhexanenitrile

Product 1

HCID 44223343(2S,3S)-3-(dibenzylamino)-2-hydroxyhexanoic acidYield 96%

Conditions

Temperature
100 °C

Procedure

To (2S,3S)-3-(dibenzylamino)-2-hydroxyhexanenitrile (93.0 g; 0.301 mol) was added 12N hydrochloric acid (465 mL). The resulting mixture was heated to reflux (100° C.) for 3 hours, monitoring progress of the reaction by TLC analysis (ethyl acetate/hexane, 1:1). After TLC analysis indicated that the reaction was complete, the reaction mixture was cooled, and the pH was adjusted to 6-7 using 6N aqueous sodium hydroxide solution (930 mL). The product was extracted with two portions of dichloromethane (2×700 mL), and the combined organic phases were dried over sodium sulfate. After filtration the solvent was removed under reduced pressure, to give 95.0 g (96%) of (2S,3S)-3-(dibenzylamino)-2-hydroxyhexanoic acid as a solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperaturethe reaction mixture was cooled
  3. extractionThe product was extracted with two portions of dichloromethane (2×700 mL)
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-e9744ddf2c58440f99eb1c3780e489a6
Source dataset
uspto-grants-2013_04
Patent number
US08431733B2

Reaction notes

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