HCID 19972455, compound → HCID 19972347, compound

HRID 1452341Notes

Reaction equation

HRID 1452341 reaction equation
CN(C)[C:3]1[CH:4]=[C:5]([C:21](=[O:40])[NH:22][CH2:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[O:38][CH3:39])[CH2:28][CH2:27]2)[C:6]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:9]([CH3:18])[C:8](=[O:19])[C:7]=2[CH:20]=1.NC1C=CC(C2OC3C([C:61](=O)[NH:62][CH2:63]CCN4CCN(C5C=CC=CC=5OC)CC4)=CC=CC=3C(=O)C=2C)=CC=1>O.[OH-].[Na+]>[CH3:61][N:62]([CH3:63])[C:15]1[CH:14]=[CH:13][C:12]([C:10]2[O:11][C:6]3[C:5]([C:21](=[O:40])[NH:22][CH2:23][CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][N:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[O:38][CH3:39])[CH2:28][CH2:27]4)=[CH:4][CH:3]=[CH:20][C:7]=3[C:8](=[O:19])[C:9]=2[CH3:18])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 19972455HCID 19972455, compoundHCID 19972731HCID 19972731, compound

Product 1

HCID 19972347HCID 19972347, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

The title compound was prepared by the same method as described for compound of Example 97, but using the compound prepared in Example 124 instead of compound of Example 94. The reaction mixture was diluted with water and 3N aqueous sodium hydroxide solution, under vigorous stirring. The precipitated solid was filtered by suction, washed with water, desiccated and purified by flash chromatography on silica gel eluting with ethyl acetate - methanol (8.5:1.5). Evaporation in vacuo of the collected fractions yielded the title compound which melted at 146°-150 (164) ° C after crystallization from acetonitrile.

Workup

  1. customThe title compound was prepared by the same method
  2. filtrationThe precipitated solid was filtered by suction
  3. washwashed with water
  4. custompurified by flash chromatography on silica gel eluting with ethyl acetate - methanol (8.5:1.5)
  5. customEvaporation in vacuo of the collected fractions

Sources & evidence

ORD record
ord-e10097d855924da9abda46ca5c4111b8
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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