Sodium Hydroxide → HCID 19374361, compound

HRID 1292355Notes

Reaction equation

HRID 1292355 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:19](=[O:20])[C:18](=[O:21])[C:17]=3[O:22]CC)[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])[CH2:30][CH:29]1[C:41]([NH2:43])=[O:42])=[O:27].[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:17](=[O:22])[C:18](=[O:21])[C:19]=3[OH:20])[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])[CH2:30][CH:29]1[C:41]([NH2:43])=[O:42])=[O:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18914179HCID 18914179, compound

Product 1

HCID 19374361HCID 19374361, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-Methoxy-4-(1-(3-ethoxy-3-cyclobutene-1,2-dion-4-yl)-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide (87 mg, 0.147 mmole) was dissolved in 3 ml of ethanol, treated with one equivalent of 1N sodium hydroxide solution, and stirred at ambient temperature overnight. All volatiles were removed under reduced pressure and the residual material was applied directly to precoated silica gel plates (0.5 mm thickness). Multiple elutions with a chloroform-methanol-acetic acid solvent mixture (80:20:2) afforded the title compound as a white solid: m.p. 144°-148° C.

Workup

  1. customAll volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-9cb180d2c74b48dd87bda5971c9352e8
Source dataset
uspto-grants-1998_05
Patent number
US05756504

Reaction notes

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