Tetrahydrofuran → HCID 86758643, compound

HRID 2298044Notes

Reaction equation

HRID 2298044 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:22]([O:24]CC)=[O:23].O.[OH-].[Li+].C(O)C.O.O1CCCC1>O>[C:22]([C:3]1[CH:4]=[C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]2)[CH:6]=[CH:7][C:2]=1[Cl:1])([OH:24])=[O:23]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrate2×HCID 19096565Water ethanolHCID 68670654HCID 68670654, compound

Product 1

HCID 86758643HCID 86758643, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 4-[4-chloro-3-(ethoxycarbonyl)phenyl]hexahydro-1H-1,4-diazepine-1-carboxylic acid, 1,1-dimethylethyl ester (Example 5a, 0.21 g), lithium hydroxide monohydrate (1.05 ml of 3M solution in water) in 1:1 ethanol/water (7 ml) was stirred at room temperature for 14 h. More lithium hydroxide monohydrate (0.55 ml of 3M solution in water) was added followed by tetrahydrofuran (1 ml). The resulting solution was stirred for 4 h at room temperature then poured into water and extracted with diethyl ether. The aqueous phase was separated, acidified with 2M hydrochloric acid and then extracted with dichloromethane three times. The combined dichloromethane layers were dried over magnesium sulfate and evaporated under reduced pressure to yield the subtitle compound as a glass.

Workup

  1. stirringThe resulting solution was stirred for 4 h at room temperature
  2. extractionextracted with diethyl ether
  3. customThe aqueous phase was separated
  4. extractionextracted with dichloromethane three times
  5. dry with materialThe combined dichloromethane layers were dried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3f6ae33081a943e5b196769acf203bd0
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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