Ethyl chloroformate → HCID 86660314, compound

HRID 453704Notes

Reaction equation

HRID 453704 reaction equation
[C:1](Cl)(=[O:5])[O:2][CH2:3][CH3:4].[Br-:7].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:42])[CH2:16][N+:17]23[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]2)[C@@H:19]([O:25][C:26](=[O:41])[C@@H:27]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:18]3)=[CH:11][CH:10]=1>C(Cl)Cl>[Br-:7].[CH2:3]([O:2][C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:42])[CH2:16][N+:17]23[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24]2)[C@@H:19]([O:25][C:26](=[O:41])[C@@H:27]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:18]3)=[CH:11][CH:10]=1)=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 86660313HCID 86660313, compound

Product 1

HCID 86660314HCID 86660314, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl carbonochloridate (10.5 μl, 0.11 mmol) was added to a solution of (R)-1-(2-(4-aminophenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (diastereomer 1 of I74) (60 mg, 0.11 mmol) in TEA (15.2 μl, 0.11 mmol) and DCM (2 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the product was purified by preparative HPLC (eluents: CH3CN/H2O) to obtain (R)-1-(2-(4-(ethoxycarbonylamino)phenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (14 mg, 20.6% yield).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe product was purified by preparative HPLC (eluents: CH3CN/H2O)

Sources & evidence

ORD record
ord-b585d1433bfd4f6d9866fd76aff22add
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

Loading…