Hydrochloric Acid → HCID 90449344, compound

HRID 1411314Notes

Reaction equation

HRID 1411314 reaction equation
C([O:3][C:4]([C:6]1([C:40]([O:42]CC)=[O:41])[CH2:9][CH:8]([CH2:10][C:11]2[CH:12]=[C:13]3[C:19]4([CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20]4)[CH2:18][N:17]([C:31]([O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])=[O:32])[C:14]3=[CH:15][CH:16]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][C:19]2([C:13]3[C:14](=[CH:15][CH:16]=[C:11]([CH2:10][CH:8]4[CH2:9][C:6]([C:4]([OH:5])=[O:3])([C:40]([OH:42])=[O:41])[CH2:7]4)[CH:12]=3)[N:17]([C:31]([O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])=[O:32])[CH2:18]2)[CH2:20]1)=[O:25])([CH3:29])([CH3:28])[CH3:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90449655HCID 90449655, compound

Product 1

HCID 90449344HCID 90449344, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-(Trimethylsilyl)ethyl) 1′-tert-butyl 5-((3,3-bis(ethoxycarbonyl)cyclobutyl)methyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (20.8 mg, 0.033 mmol) was dissolved in ethanol (1 mL). Thereafter, an 8 N aqueous solution of sodium hydroxide (0.5 mL) was added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at room temperature for 4 hours. Thereafter, a 1 N aqueous solution of hydrochloric acid was added to the reaction solution, and the thus obtained mixture was neutralized and was then extracted with chloroform. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo, to obtain 3-((1′-(tert-butoxycarbonyl)-1-((2-(trimethylsilyl)ethoxy) carbonyl)spiro[indoline-3,3′-pyrrolidin]-5-yl)methyl)cyclobutane-1,1-dicarboxylic acid (19.3 mg, quant.) in the form of a colorless oily product.

Workup

  1. temperatureunder cooling on ice
  2. extractionwas then extracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-dba6377a777c4c17b1124df217b3ec0e
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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