Sodium Hydroxide → (3-Oxo-1-phenyl-1,4-diazaspiro[5.5]undec-4-yl)acetic acid

HRID 1894862Notes

Reaction equation

HRID 1894862 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9]([O:11]CC)=[O:10])[CH2:6][C:5]2([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:3]1.[OH-].[Na+].O=C1NCC2(CCCCC2)N(C2C=CC=CC=2)C1CC(O)=O>O1CCCC1>[O:1]=[C:2]1[N:7]([CH2:8][C:9]([OH:11])=[O:10])[CH2:6][C:5]2([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[N:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 68633030(3-Oxo-1-phenyl-1,4-diazaspiro[5.5]undecyl)acetic acidHCID 86646979Ethyl (3-oxo-1-phenyl-1,4-diazaspiro[5.5]undec-4-yl)acetate

Product 1

HCID 68631156(3-Oxo-1-phenyl-1,4-diazaspiro[5.5]undec-4-yl)acetic acidYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an analogous manner to Example 2(e), by reaction of 220 mg (0.66 mmol) of ethyl (3-oxo-1-phenyl-1,4-diazaspiro[5.5]undec-4-yl)acetate with 130 mg (3.25 mmol) of sodium hydroxide in 10 ml of tetrahydrofuran, 180 mg of (3-oxo-1-phenyl-1,4-diazaspiro[5.5]undecyl)acetic acid are obtained in the form of a beige solid. M.p. 167-9° C., yield=89%.

Workup

  1. customare obtained in the form of a beige solid

Sources & evidence

ORD record
ord-811cd9296a3a47fca68bbc58fcee5c93
Source dataset
uspto-grants-2013_08
Patent number
US08513307B2

Reaction notes

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