Hydrochloric Acid → Z-L-Dap(boc)-OL

HRID 1934684Notes

Reaction equation

HRID 1934684 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]([NH:13][C@@H:14]([CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:15](OC)=[O:16])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>CO>[CH2:3]([O:10][C:11]([NH:13][C@@H:14]([CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][OH:16])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10831821(S)-Methyl 2-N-Cbz-3-N-Boc-propanoate

Product 1

HCID 10734767Z-L-Dap(boc)-OLYield 87.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (251 mg) was added to a solution of methyl (S)-2-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)propionate (1.17 g) in methanol (10 mL) at 0° C. The mixture was stirred for an hour at the same temperature and then for an hour at ambient temperature. After addition of 3.6% hydrochloric acid, the mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and an aqueous saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residual crystals were suspended in hot diisopropyl ether and cooled to ambient temperature with stirring. The residual crystals were collected by filtration and washed with diisopropyl ether to give (S)-2-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)propanol (945 mg) as white crystals.

Workup

  1. waitfor an hour at ambient temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. stirringwith stirring
  8. filtrationThe residual crystals were collected by filtration
  9. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-0aecf78bada94441b8d0ee88e232c06d
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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