Methanol → (S)-Methyl 2-N-Cbz-3-N-Boc-propanoate

HRID 726424Notes

Reaction equation

HRID 726424 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[CH3:27]CN=C=NCCCN(C)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[CH3:27][O:14][C:13](=[O:15])[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

6

Reactant 3

HCID 887MethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2756240L-N-Cbz-3-N-Boc-Amino-alanine

Product 1

HCID 10831821(S)-Methyl 2-N-Cbz-3-N-Boc-propanoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The product (0.867 g) obtained in the above (2) is dissolved in dichloromethane (15 ml), and thereto are added methanol (1.5 ml), 4-dimethylaminopyridine (34 mg) and WSC.HCl (0.633 g) under ice-cooling. The mixture is stirred under ice-cooling for two hours, and then stirred at room temperature for 12 hours. The mixture is concentrated under reduced pressure to the volume of about 5 ml, and the residue is poured into water. The mixture is extracted three time with ethyl acetate, and the organic layer is washed 1N HCl (twice), a saturated aqueous sodium hydrogen carbonate solution (twice), and with a saturated brine (twice), and then dried over anhydrous magnesium sulfate. The desiccant is removed by filtration, and the filtrate is concentrated under reduced pressure to give the title compound (0.875 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for two hours
  3. stirringstirred at room temperature for 12 hours
  4. concentrationThe mixture is concentrated under reduced pressure to the volume of about 5 ml
  5. additionthe residue is poured into water
  6. extractionThe mixture is extracted three time with ethyl acetate
  7. washthe organic layer is washed 1N HCl (twice), a saturated aqueous sodium hydrogen carbonate solution (twice), and with a saturated brine (twice), and
  8. dry with materialthen dried over anhydrous magnesium sulfate
  9. customThe desiccant is removed by filtration
  10. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-0a24c82ff362497c92f30afb38e000cd
Source dataset
uspto-grants-1998_01
Patent number
US05707994

Reaction notes

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