Water → HCID 7019700, compound

HRID 487863Notes

Reaction equation

HRID 487863 reaction equation
[NH2:1][C@@H:2]([CH2:6][NH2:7])[C:3]([OH:5])=[O:4].Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[CH2:19]([O:21][CH2:22][CH3:23])C.[OH2:24]>C1(C)C=CC=CC=1.[OH-].[Na+]>[CH2:12]([O:11][C:9]([NH:1][C@@H:2]([CH2:6][NH:7][C:19]([O:21][CH2:22][C:23]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1)=[O:24])[C:3]([OH:5])=[O:4])=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 10387Benzyl chloroformate2×HCID 97328L-alpha,beta-Diaminopropionic acid

Product 1

HCID 7019700HCID 7019700, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 14798Sodium HydroxideSolvent2×

Procedure

In an ice-water bath, to 2(S),3-diamino-propionic acid (32 g) in water (1000 mL) add, with stirring, concurrently solutions of benzyl chloroformate (76 mL) in toluene (20 mL) and 4N NaOH (133 mL) over 30 min. Stir at 20°-25° C. for 45 min and then add additional benzyl chloroformate (34 mL) in toluene (10 mL) and 4N NaOH (61 mL) concurrently over 10 min. Stir the mixture at ambient temperature for 2 hr. Add diethyl ether (Et2O) (200 mL) and stir for 10 min. Filter and was the solid with Et2O (200 mL). Extract the aqueous solution with Et2O. Combine the aqueous solution with the solid and add concentrated HCl to pH 1-2. Extract the aqueous solution with EtOAc (250 mL twice). Dry the EtOAc extract (MgSO4) then concentrate in vacuo to give 2(S),3-bis-(benzyloxycarbonylamino)propionic acid, [α]23.6D =-13.7° (MeOH).

Workup

  1. stirringStir at 20°-25° C. for 45 min
  2. stirringStir the mixture at ambient temperature for 2 hr
  3. filtrationFilter
  4. extractionExtract the aqueous solution with Et2O
  5. additionadd concentrated HCl to pH 1-2
  6. extractionExtract the aqueous solution with EtOAc (250 mL twice)
  7. dry with materialDry the EtOAc
  8. extractionextract (MgSO4)
  9. concentrationthen concentrate in vacuo

Sources & evidence

ORD record
ord-2bca7d92e7884f5cb9a28448e87658cc
Source dataset
uspto-grants-1994_03
Patent number
US05298492

Reaction notes

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