Ethyl chloroformate → HCID 140376332, compound

HRID 1489477Notes

Reaction equation

HRID 1489477 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].Cl.[C:8]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH2:17][NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12]1)(=[NH:10])[NH2:9].[OH-].[Na+]>C(Cl)Cl>[CH2:5]([O:4][C:2]([NH:10][C:8](=[NH:9])[N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH2:17][NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12]1)=[O:3])[CH3:6]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 86748617HCID 86748617, compound

Product 1

HCID 140376332HCID 140376332, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.55 ml of ethyl chloroformate is added dropwise to a solution of 2.0 g of benzyl [[(S)-1-amidino-3-piperidinyl]methyl]carbamate hydrochloride in 200 ml of methylene chloride. The reaction mixture is cooled to 0°. 113 ml of 0.1N sodium hydroxide solution are added dropwise while stirring. Subsequently, the mixture is stirred in an ice bath. The phases are separated. The organic phase is washed with water, dried and evaporated. There are obtained 1.5 g of benzyl (S)-1-(ethoxycarbonylamino-imino-methyl)-piperidin-3-ylmethylcarbamate, MS (FAB): 363.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture is cooled to 0°
  2. stirringSubsequently, the mixture is stirred in an ice bath
  3. customThe phases are separated
  4. washThe organic phase is washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-a251f885e25d47319e7642cf897856e8
Source dataset
uspto-grants-1997_10
Patent number
US05677448

Reaction notes

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