Dimethylformamide → 1-(N-benzyloxycarbonyl-L-valyloxy)-2-methyl-2-propanol

HRID 989963Notes

Reaction equation

HRID 989963 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:34][C:35]([OH:39])([CH3:38])[CH2:36]O.CN(C=O)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:34][C:35]([CH3:38])([OH:39])[CH3:36])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 684102-Methylpropane-1,2-diolHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 540342421-(N-benzyloxycarbonyl-L-valyloxy)-2-methyl-2-propanolYield 88.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

N-Benzyloxycarbonyl-L-valine (2.02 g, 8.0 mmol), 4-dimethylaminopyridine (100 mg, 0.8 mmol), and), and dicyclohexylcarbodiimide (2.04 g, 9.9 mmol, in 20 mL CH2Cl2) were added to 2-methyl-1,2-propanediol (12.2 mmol) in 30 mL dry CH2Cl2, with cooling in an ice bath. DMF (5 mL) was added. After stirring for 5 h at 10° C., the reaction mixture was filtered, concentrated, and then redissolved in ethyl acetate. The organic solution was washed with saturated NaCl, dried over anhydrous Na2SO4, and concentrated. Flash column chromatography (silica, 2/1 petroleum ether-ethyl acetate) gave 2.3 g of the title compound.

Workup

  1. temperaturewith cooling in an ice bath
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. dissolutionredissolved in ethyl acetate
  5. washThe organic solution was washed with saturated NaCl
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d6c572f8a0884a948d9d3282f74168f4
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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