Ethyl chloroformate → HCID 22624265, compound

HRID 279054Notes

Reaction equation

HRID 279054 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][C:8]1[CH:28]=[CH:27][C:11]([C:12]([C:14]2[N:15]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:16]=[CH:17][CH:18]=2)=[O:13])=[CH:10][CH:9]=1>N1C=CC=CC=1>[CH2:5]([O:4][C:2]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([C:14]2[N:15]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:25])[CH3:26])[CH:16]=[CH:17][CH:18]=2)=[O:13])=[CH:27][CH:28]=1)=[O:3])[CH3:6]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 22624249HCID 22624249, compound

Product 1

HCID 22624265HCID 22624265, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl chloroformate (0.21 g, 1.95 mM) was added dropwise to a stirred solution of 2-(4-aminobenzoyl)-1-(2-trimethylsilylethoxymethyl)pyrrole (0.5 g. 1.58 mM) in pyridine (5 ml) at 5° C. After 5 minutes the cooling bath was removed and stirring continued for 1.75 hours. The mixture was treated with MeOH (2 ml) and evaporated and the residue partitioned between EtOAc and aqueous sodium bicarbonate solution. The organic layer was washed with water, aqueous citric acid, dried (MgSO4) and evaporated. to give 2-(4-ethoxycarbonylaminobenzoyl)-1-(2-trimethylsilylethoxymethyl)pyrrole as an oil (0.58 g). MS: 389 (MH+). NMR: 0.0 (9H, s); 0.89 (2H, t); 1.38 (3H, t) 3.57 (2H, t); 4.28 (2H, q); 5.8 (2H, s); 6.34 (1H, m); 6.82 (1H, m); 7.50 (1H, m); 7.7 (2H, d); 7.83 (2H, d); 10.1 (1H, br s).

Workup

  1. customAfter 5 minutes the cooling bath was removed
  2. additionThe mixture was treated with MeOH (2 ml)
  3. customevaporated
  4. customthe residue partitioned between EtOAc and aqueous sodium bicarbonate solution
  5. washThe organic layer was washed with water, aqueous citric acid
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-908d8c98a5004e179f31212e2d689406
Source dataset
uspto-grants-2002_03
Patent number
US06362191B1

Reaction notes

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