Hydrochloric Acid → (2R)-2-Amino-3-hydroxy-N-(phenylmethyl)propanamide

HRID 74115Notes

Reaction equation

HRID 74115 reaction equation
[CH2:1]([NH:8][C:9](=[O:21])[C@H:10]([NH:13]C(OC(C)(C)C)=O)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.Cl.[OH-].[Na+]>O>[NH2:13][C@H:10]([CH2:11][OH:12])[C:9]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 46223140tert-butyl N-[(1R)-1-(benzylcarbamoyl)-2-hydroxyethyl]carbamate

Product 1

HCID 10655432(2R)-2-Amino-3-hydroxy-N-(phenylmethyl)propanamideYield 73.52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 mL four-neck round bottom flask, 34.0 g (R)-N-benzyl-2-(tert-butoxycarbonylamino)-3-hydroxypropionamide and 350 mL dichloromethane were added, and the mixture was stirred to obtain a clear solution. At 20-25° C., 40.0 g concentrated hydrochloric acid (having a mass concentration of 36.0%) was added, and the reaction was continued. TLC tracking was performed, till the raw materials were completely converted. After the reaction was completed, the temperature was decreased to 20° C. The mixture was suction-filtered, to obtain a white needle-like crystal. The obtained white crystalline solid was dissolved in 50 g water. At 20-25° C., 30% sodium hydroxide solution was added to adjust the pH value of the system to 8-9. After the addition, the solution was stirred continuously, and a white flaky crystal was precipitated. The mixture was suction-filtered, and the filter was washed and dried, to obtain a target product of 16.5 g (0.085 mol). The molar yield was 73.52%.

Workup

  1. customto obtain a clear solution
  2. customAt 20-25° C.
  3. additionwas added
  4. customwas decreased to 20° C
  5. filtrationThe mixture was suction-filtered
  6. customto obtain a white needle-like crystal
  7. additionAfter the addition
  8. stirringthe solution was stirred continuously
  9. customa white flaky crystal was precipitated
  10. filtrationThe mixture was suction-filtered
  11. washthe filter was washed
  12. customdried
  13. customto obtain a target product of 16.5 g (0.085 mol)

Sources & evidence

ORD record
ord-2fc6ac5f6b8c4ae491efb78357efebdf
Source dataset
uspto-grants-2014_09
Patent number
US08829226B2

Reaction notes

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