Ethylene Glycol → HCID 11175806, compound

HRID 1870261Notes

Reaction equation

HRID 1870261 reaction equation
C(C[C@@H:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:7][CH2:6][CH2:5]1)#N.[OH-:25].[K+].Cl.[CH2:28]([OH:31])[CH2:29]O>>[C:28]([CH2:29][C@@H:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH2:7][CH2:6][CH2:5]1)([OH:31])=[O:25]

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 54536415HCID 54536415, compound

Product 1

HCID 11175806HCID 11175806, compound

Conditions

Temperature
172.5 °C

Procedure

A mixture of (5R)-5-cyanomethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (102 mg), potassium hydroxide (84 mg) and ethylene glycol (2 ml) is heated with stirring at 170-175° C. for 6 hours. The reaction solution is acidified with conc. hydrochloric acid, extracted with ethyl acetate, dried over sodium sulfate, and the resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol;=9:1) to give (5R)-5-carboxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (108 mg).

Workup

  1. temperatureis heated
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customthe resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol;=9:1)

Sources & evidence

ORD record
ord-e5c9740fac2a4717bd12972ee673e2bd
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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