tert-Butyl 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-oxopropanoate → HCID 23458743, compound

HRID 1680010Notes

Reaction equation

HRID 1680010 reaction equation
[CH:1]([CH:3]([N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=O.Cl.Cl.[NH2:24][CH:25]([C:29]1([SH:36])[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]1)[C:26]([OH:28])=[O:27].C([O-])(=O)C.[Na+]>C(O)C.O>[C:26]([CH:25]1[C:29]2([CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]2)[S:36][CH:1]([CH:3]([N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[NH:24]1)([OH:28])=[O:27]

Participants

6

Reactant 3

HCID 289594tert-Butyl 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-oxopropanoateHCID 517045Sodium AcetateHCID 86737763HCID 86737763, compound

Product 1

HCID 23458743HCID 23458743, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 166.9 g (0.57 mole) of tert-butyl 2-formyl-2-phthalimido-acetate in 1150 ml of ethanol, preheated to 60° C., there is added a solution of 160 g (0.57 mole) of alpha-amino-4-mercapto-1-methyl-4-piperidineacetic acid dihydrochloride and 235.6 g (1.73 mole) of sodium acetate (crystallized with three molecules of water) dissolved in 1150 ml of water. The reaction mixture is stirred for about ten minutes and then left to stand for 24 hours. The precipitate is filtered off, washed with water and dried. 223 g of the gamma-isomer of tert-butyl 4-carboxy-8-methyl-alpha-phthalimido-1-thia-3,8-diazaspiro-[4.5]decane-2-acetate is obtained; Yield: 81%; M.P. 276°-278° C. (decomposition).

Workup

  1. custompreheated to 60° C.
  2. waitleft
  3. filtrationThe precipitate is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-667344c6e8804c98a4d1075db2ae5bcd
Source dataset
uspto-grants-1981_06
Patent number
US04271172

Reaction notes

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