Hydrochloric Acid → HCID 57693709, compound

HRID 20203Notes

Reaction equation

HRID 20203 reaction equation
C[O:2][C:3]([CH:5]1[CH2:12][CH:11]2[N:13]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:7]([CH2:8][CH:9]([O:19][C:20]([C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)=[O:21])[CH2:10]2)[CH2:6]1)=O.CC(C)([O-])C.[K+].CCOC(C)=O.CO.Cl>C1COCC1.O>[CH3:18][O:17][C:15]([CH:14]1[C:3](=[O:2])[CH:5]2[CH2:12][CH:11]3[CH2:10][CH:9]([O:19][C:20]([C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[NH:24][CH:23]=4)=[O:21])[CH2:8][CH:7]([CH2:6]2)[N:13]13)=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21584119Ethylacetate methanolHCID 23665647Potassium tert-butoxideHCID 576937077-(1H-Indole-3-carbonyloxy)-9-methoxycarbonylmethyl-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

Product 1

HCID 57693709HCID 57693709, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

7-(1H-Indole-3-carbonyloxy)-9-methoxycarbonylmethyl-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester (4.87 gr, 11.75 mmol) dissolved in THF (150 mL) is added to a mixture of potassium tert-butoxide (5.26 gr, 46.9 mmol) in THF (150 mL), under nitrogen. The resulting suspension is stirred for 3 h, until the starting product has been used up as shown by thin-layer chromatography (AcOEt/MeOH 9:1). When the reaction is considered completed, water is added and the pH adjusted to 7.5 with 1 M hydrochloric acid. The product is extracted with dichloromethane, and the organic phase is dried and evaporated, to provide 5-(1H-Indole-3-carbonyloxy)-10-oxo-8-aza-tricyclo[5.3.1.03,8]undecane-9-carboxylic acid methyl ester as a solid (3.63 gr, 81%).

Workup

  1. extractionThe product is extracted with dichloromethane
  2. customthe organic phase is dried
  3. customevaporated

Sources & evidence

ORD record
ord-49de88fa76874548af65813e4432c33d
Source dataset
uspto-grants-2010_06
Patent number
US07745628B2

Reaction notes

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