Pyridine → HCID 56979540, compound

HRID 1170638Notes

Reaction equation

HRID 1170638 reaction equation
[NH2:1][C:2]([CH3:23])([CH3:22])[CH2:3][O:4][C:5](=[O:21])[C@H:6]([CH:18]([CH3:20])[CH3:19])[NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].N1C=CC=CC=1.Cl[C:31]([O:33][CH2:34][Cl:35])=[O:32]>ClCCl>[Cl:35][CH2:34][O:33][C:31]([NH:1][C:2]([CH3:23])([CH3:22])[CH2:3][O:4][C:5](=[O:21])[C@H:6]([CH:18]([CH3:19])[CH3:20])[NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62754Chloromethyl chloroformateHCID 54456052HCID 54456052, compound

Product 1

HCID 56979540HCID 56979540, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-2-methyl-1-(N-benzyloxycarbonyl-L-valyloxy)-propane (2.9 g, 9 mmole) and pyridine (2 ml) in dichloromethane (50 ml) was added chloromethyl chloroformate (1.55 g, 12 mmole) and the mixture was stirred for 3 hours at room temperature. The mixture was evaporated under reduced pressure and ethyl acetate was added. The organic phase was washed with water, dried with sodium sulfate and evaporated under reduced pressure. The product was isolated by silica gel column chromatography with hexane/ethyl acetate. Yield: 1.1 g=29%.

Workup

  1. customThe mixture was evaporated under reduced pressure and ethyl acetate
  2. additionwas added
  3. washThe organic phase was washed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe product was isolated by silica gel column chromatography with hexane/ethyl acetate

Sources & evidence

ORD record
ord-a4ba3cbfb3524aae9bbbaea80ffac785
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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