Hydrochloric Acid → HCID 90449461, compound

HRID 1411315Notes

Reaction equation

HRID 1411315 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]2([C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][CH:22]4[CH2:25][C:24](C(O)=O)([C:26]([OH:28])=[O:27])[CH2:23]4)[CH:19]=3)[N:14]([C:32]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])=[O:33])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[OH-].[Na+].Cl>O1CCCC1.C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]2([C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][CH:22]4[CH2:25][CH:24]([C:26]([OH:28])=[O:27])[CH2:23]4)[CH:19]=3)[N:14]([C:32]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])=[O:33])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 90449344HCID 90449344, compound

Product 1

HCID 90449461HCID 90449461, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-((1′-(tert-Butoxycarbonyl)-1-((2-(trimethylsilyl)ethoxy)carbonyl)spiro[indoline-3,3′-pyrrolidin]-5-yl)methyl)cyclobutane-1,1-dicarboxylic acid (19.0 mg, 0.033 mmol) was dissolved in tetrahydrofuran (1 mL). Thereafter, carbonyldiimidazole (6.0 mg, 0.037 mmol) was added to the above obtained solution at room temperature, and the thus obtained mixture was then stirred for 1.5 hours. Thereafter, the reaction solution was concentrated in vacuo, and the obtained reaction mixture was then dissolved in ethanol (1 mL). Subsequently, 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 18 hours. Thereafter, a 1 N aqueous solution of hydrochloric acid was added to the reaction solution. 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, so as to obtain 3-((1′-(tert-butoxycarbonyl)-1-((2-(trimethylsilyl)ethoxy)carbonyl)spiro[indoline-3,3′-pyrrolidin]-5-yl)methyl)cyclobutanecarboxylic acid (17.3 mg, 99%) in the form of a brown oily product.

Workup

  1. concentrationThereafter, the reaction solution was concentrated in vacuo
  2. customthe obtained reaction mixture
  3. temperatureunder cooling on ice
  4. stirringthe thus obtained mixture was then stirred at room temperature for 18 hours
  5. extractionwas then extracted with chloroform
  6. washThe organic layer was washed with brine
  7. dry with materialwas then dried over anhydrous sodium sulfate
  8. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-6cdf800291044f7f8bf8c30463816bcb
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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