Acetic Acid → HCID 59625185, compound

HRID 2192857Notes

Reaction equation

HRID 2192857 reaction equation
Cl.[C:2]([O:6][C:7]([NH:9][CH2:10][C@@H:11]([C:13]([O:15][CH3:16])=[O:14])[NH2:12])=[O:8])([CH3:5])([CH3:4])[CH3:3].[CH3:17][CH:18]([CH3:21])[CH:19]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CO>[C:2]([O:6][C:7]([NH:9][CH2:10][C@@H:11]([C:13]([O:15][CH3:16])=[O:14])[NH:12][CH2:17][CH:18]([CH3:21])[CH3:19])=[O:8])([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 18334328methyl (2S)-2-amino-3-{[(tert-butoxy)carbonyl]amino}propanoate hydrochloride

Product 1

HCID 59625185HCID 59625185, compound

Reagents, catalysts & solvents 1

HCID 22134543HCID 22134543, compoundSolvent

Procedure

Methyl 3-[(tert-butoxycarbonyl)amino]-L-alaninate hydrochloride (2.00 g), 2-methylpropanal (860 μl) and acetic acid (450 μl) were dissolved in 1,2-dichloroethane-methanol (5:1, 60 ml), and the mixture was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (4.00 g) was added and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (0:1-1:0) was concentrated under reduced pressure to give the object compound (1.76 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washthe fraction eluted with ethyl acetate-hexane (0:1-1:0)
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-e60290dd17c44cf098400cefedcd59a0
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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