Dicyclohexylcarbodiimide → 2,2-dimethoxyethyl N-benzyloxycarbonyl-L-prolinate

HRID 844515Notes

Reaction equation

HRID 844515 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][CH:21]([O:24][CH3:25])[CH2:22]O.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([O:15][CH2:22][CH:21]([O:24][CH3:25])[O:20][CH3:19])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 101987Benzyloxycarbonyl-L-prolineHCID 5423812,2-Dimethoxyethanol

Product 1

HCID 701608922,2-dimethoxyethyl N-benzyloxycarbonyl-L-prolinateYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 100 mL, round bottom flask equipped with a magnetic stirrer and nitrogen inlet is added N-Benzyloxycarbonyl-L-proline (3.5 g), dichloromethane (25 mL) and 2,2-dimethoxyethanol (1.8 g). The mixture is cooled using an ice bath (0-5° C.) and DMAP (86 mg) is added. DCC (3.06 g) is added to the mixture over a period of 2 minutes. The resulting precipitate is filtered, washed with heptanes (2×10 mL) and the filtrate is concentrated under reduced pressure. The residue was purified by silica gel chromatography using heptanes/ethyl acetate (4:1) as the eluent, and 4.5 g of 2,2-dimethoxyethyl N-benzyloxycarbonyl-L-prolinate was obtained.

Workup

  1. customTo a 100 mL, round bottom flask equipped with a magnetic stirrer and nitrogen inlet
  2. temperatureThe mixture is cooled
  3. additionis added
  4. filtrationThe resulting precipitate is filtered
  5. washwashed with heptanes (2×10 mL)
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9b1351d4a3a14ae8a7fe3543b9bdc94b
Source dataset
uspto-grants-2002_04
Patent number
US06380388B1

Reaction notes

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