HCID 522608, compound → HCID 56606204, compound

HRID 1156829Notes

Reaction equation

HRID 1156829 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10](=[O:11])[NH:9][C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[CH:16][C:7]=12)=[O:5])[CH3:2].[Na].[CH3:18][O:19][C:20](=[O:28])[CH:21](Br)[CH2:22][C:23]([O:25][CH3:26])=[O:24]>CN(C=O)C.O>[CH3:18][O:19][C:20](=[O:28])[CH:21]([N:9]1[C:10](=[O:11])[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=[C:8]12)[CH2:22][C:23]([O:25][CH3:26])=[O:24]

Participants

6

Reactant 3

HCID 522608HCID 522608, compoundHCID 5360545SodiumHCID 10353288Cyclohepta[b]pyrrole-3-carboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester

Product 1

HCID 56606204HCID 56606204, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1,2-dihydro-2-oxocyclohepta[b]pyrrole-3-carboxylic acid ethyl ester, sodium salt (12.5 g, described in example 1) and 2-bromobutanedioic acid dimethyl ester (14.5 g) in DMF (14.5 g) was heated at 100° C. for 48 hr. The mixture was cooled, diluted with water and extracted with chloroform. The chloroform extract was passed through a column of silica gel. Subsequent elution of the column with chloroform-methanol (97:3) gave 2.0 g of 2-(3-ethoxycarbonyl-1,2-dihydro-2-oxocyclohepta[b]pyrrol-1-yl) butanedioic acid dimethyl ester, nmr (CDCl3) δ1.4 (t, 3H), 3.35 (m, 2H), 3.6 and 3.7 (2s, 6H), 4.4 (q, 2H), 5.6 (t, 1H), 7.45 (m, 4H), 9.05 (d, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with chloroform
  3. extractionThe chloroform extract
  4. washSubsequent elution of the column with chloroform-methanol (97:3)

Sources & evidence

ORD record
ord-8e4930cbb09c403098dcb7afc892f15d
Source dataset
uspto-grants-1982_06
Patent number
US04337265

Reaction notes

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