Sodium Hydroxide → 2-(1-Tert-butoxycarbonyl-5-oxo-azepan-4-YL)acetic acid

HRID 239161Notes

Reaction equation

HRID 239161 reaction equation
[OH-].[Na+].C(OC([C:8]1([CH2:23][C:24]([O:26]CC)=[O:25])[C:14](=[O:15])[CH2:13][CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:9]1)=O)C>O.C1COCC1>[C:19]([O:18][C:16]([N:11]1[CH2:12][CH2:13][C:14](=[O:15])[CH:8]([CH2:23][C:24]([OH:26])=[O:25])[CH2:9][CH2:10]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 866860534-Ethoxycarbonylmethyl-5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Product 1

HCID 834890002-(1-Tert-butoxycarbonyl-5-oxo-azepan-4-YL)acetic acidYield 65.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

23.3 g sodium hydroxide in 218 mL water was added to 38 g 4-ethoxycarbonylmethyl-5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester in 155 mL THF. The reaction was stirred over night at RT, THF was removed and the mixture was extracted with dichlormethane. The aqueous part was acidified with 3M HCl to pH 3 at 0° C. The aqueous solution was extracted with dichloromethane, dried over magnesium sulfate, concentrated under reduced pressure to give 18.2 g of the desired product. (M+H)+=272

Workup

  1. customTHF was removed
  2. extractionthe mixture was extracted with dichlormethane
  3. customwas acidified with 3M HCl to pH 3 at 0° C
  4. extractionThe aqueous solution was extracted with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e0c6f6c2aab4b7684b45f69e503a4b2
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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