Sodium Hydroxide → HCID 10693020, compound

HRID 2292790Notes

Reaction equation

HRID 2292790 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]([S:25][CH3:26])=[C:12]2[CH2:27][C:28]([NH2:30])=[O:29])C.[OH-].[Na+]>C1COCC1.CCO>[NH2:30][C:28](=[O:29])[CH2:27][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:31])=[O:3])[CH:10]=2)[N:14]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]=1[S:25][CH3:26]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10622985HCID 10622985, compound

Product 1

HCID 10693020HCID 10693020, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

As described in Example 45, 245 mg (0.56 mmol) of 4-[[3-(2-amino-2-oxoethyl)-2-(methylthio)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl ester (Example 47) was hydrolyzed with 1 mL of 5N NaOH in 5 mL of THF and 15 mL of EtOH. The crude product was washed with EtOH/ether to give 195 mg (85% yield of 4-[[3-(2-amino-2-oxoethyl)-2-(methylthio)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid, mp, 187°-188° C.

Workup

  1. washThe crude product was washed with EtOH/ether

Sources & evidence

ORD record
ord-09c8dab85ecc4cb0bbfb3a5909fc0c37
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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