1,2-Dichloroethane → (S)-3-amino-2-hydroxy-pentanoic acid benzylamide

HRID 2212222Notes

Reaction equation

HRID 2212222 reaction equation
C(OC([NH:8][CH:9]([CH2:15][CH3:16])[CH:10]([OH:14])[C:11]([OH:13])=O)=O)(C)(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CN1CCOCC1>ClCCl>[CH2:31]([NH:38][C:11](=[O:13])[C@@H:10]([OH:14])[CH:9]([NH2:8])[CH2:15][CH3:16])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 219627633-{[(Tert-butoxy)carbonyl]amino}-2-hydroxypentanoic acid

Product 1

HCID 69433021(S)-3-amino-2-hydroxy-pentanoic acid benzylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-tert-Butoxycarbonylamino-2-hydroxy-pentanoic acid (300 mg, 1.2 9 mmol) was combined with EDC (400 mg, 2.1 mmol) and HOBt (400 mg, 2.6 mmol). A solution of benzylamine (0.22 mL) and 4-methylmorpholine (0.5 mL) in dichloromethane (4 mL) was added in one portion. The reaction mixture was stirred at ambient temperature for 2 h. After dilution with ethyl acetate (150 mL), the solution was washed with 1 N aqueous HCl, water, saturated aqueous NaHCO3 solution and brine. The resultant mixture was dried with magnesium sulfate and evaporated under vacuum to yield (S)-3-amino-2-hydroxy-pentanoic acid benzylamide (380 mg) as a white solid.

Workup

  1. washAfter dilution with ethyl acetate (150 mL), the solution was washed with 1 N aqueous HCl, water, saturated aqueous NaHCO3 solution and brine
  2. dry with materialThe resultant mixture was dried with magnesium sulfate
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-c778ca662b274a7cbe377f1c637f5191
Source dataset
uspto-grants-2006_09
Patent number
US07101880B2

Reaction notes

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