Pyridine → HCID 69945746, compound

HRID 341778Notes

Reaction equation

HRID 341778 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]=[C:10]([CH2:13][CH:14]([NH2:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[Cl:27][C:28]([Cl:35])([Cl:34])[CH2:29][O:30][C:31](Cl)=[O:32]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]=[C:10]([CH2:13][CH:14]([NH:20][C:31]([O:30][CH2:29][C:28]([Cl:35])([Cl:34])[Cl:27])=[O:32])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 54214257HCID 54214257, compound

Product 1

HCID 69945746HCID 69945746, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 214 mg (0.75 mmol) 3-(2-amino-2-ethoxycarbonyl-ethyl)-2,5-dihydropyrrole-1-carboxylic acid tert.-butylester and 119 mg (1.5 mmol) pyridine in 2 ml methylene chloride was added a small amount of DMAP followed by 212 mg (1mmol) 2,2,2-trichloroethoxycarbonyl chloride. The mixture was allowed to warm to room temperature overnight. The mixture was diluted with ether, washed with water, sat. CuSO4, water and brine, dried over MgSO4 and evaporated. Purification of the residue by flash-chromatography (elution with petrol ether/ethyl acetate 3:1) gave 320 mg (93%) 3 -[2-(2,2,2-trichloroethoxycarbonyl-amino)-2-ethoxycarbonyl-ethyl]-2,5-dihydropyrrole-1-carboxylic acid tert.-butylester as a colorless oil, which was immediately used for the next step.

Workup

  1. washwashed with water, sat. CuSO4, water and brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customPurification of the residue
  5. washby flash-chromatography (elution with petrol ether/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-c693392b2c094f0ba1805f8a8d5cff92
Source dataset
uspto-grants-1999_01
Patent number
US05856309

Reaction notes

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