Ethyl chloroformate → HCID 140376332, compound

HRID 1901817Notes

Reaction equation

HRID 1901817 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-59f4fb9d977f4865a0f7a164f63ddfcf
Source dataset
uspto-grants-1996_11
Patent number
US05578594

Reaction notes

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