HCID 54440772, compound → HCID 20077534, compound

HRID 1655053Notes

Reaction equation

HRID 1655053 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]4[CH:33]=[CH:32][C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]=4)=[CH:18][CH:17]=3)=[CH:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)=[O:4]>[OH-].[Na+].O1CCCC1.CO.O>[CH3:14][N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:13]=2)[C:9]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[CH:20][CH:21]=2)=[CH:10]1

Participants

6

Reactant 1

HCID 54440772HCID 54440772, compound

Product 1

HCID 20077534HCID 20077534, compoundYield 59.7%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of the methyl ester (Example 10, part ii) (1.73 g) in aqueous sodium hydroxide (2M, 5.9 ml), tetrahydrofuran (20 ml) and methanol (10 ml) was refluxed with stirring overnight. The reaction mixture was cooled, diluted with water until turbid and washed with diethyl ether (2×). The aqueous phase was acidified with acetic acid and the resulting precipitate filtered, washed with water and dried in vacuo at 50° C. to give the product as a white solid (1 g). A small amount was crystallised from tetrahydrofuran/ethanol m.p. 208°-212° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with diethyl ether (2×)
  3. filtrationthe resulting precipitate filtered
  4. washwashed with water
  5. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-11841f544d40485eaefa555b93fd970f
Source dataset
uspto-grants-1995_04
Patent number
US05410061

Reaction notes

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