1,2-Dichloroethane → HCID 19437233, compound

HRID 1735462Notes

Reaction equation

HRID 1735462 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:17])([CH2:13][CH2:14][CH2:15][OH:16])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1([CH3:17])[CH2:13][CH2:14][CH2:15][O:16][C:10]1=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 111,2-DichloroethaneHCID 19437231N-[(1,1-Dimethylethoxy)carbonyl]-5-hydroxy-2-methylnorvaline

Product 1

HCID 19437233HCID 19437233, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(t-Butyloxycarbonyl)amino-2-methyl-5-hydroxypentanoic acid (3.0 g, 0.012 mol) and EDC (2.56 g, 0.013 mol) were dissolved in DMF (20 mL) and stirred at ambient temperature for 18 h. The reaction mixture was concentrated to dryness, and the residue was partitioned between EtOAc (30 mL)-H2O (30 mL), the organic layer separated, washed with brine and dried (Na2SO4). Filtration, concentration, and chromatography (SiO2, EtOAc: hexane, 1:3) gave 0.86 g (31%) of the title compound. 1H NMR (CDCl3) δ5.1 (br s, 1H), 4.35-4.55 (m, 2H), 2.49-2.64 (m, 1H), 1.78-2.1 (m, 3H), 1.45 (s, 3H), 1.41 (s, 9H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was partitioned between EtOAc (30 mL)-H2O (30 mL)
  3. customthe organic layer separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationFiltration, concentration, and chromatography (SiO2, EtOAc: hexane, 1:3)

Sources & evidence

ORD record
ord-3f9cc4162c624f3c808b2f72b2cae652
Source dataset
uspto-grants-1996_07
Patent number
US05536750

Reaction notes

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