Water → HCID 68154521, compound

HRID 1615769Notes

Reaction equation

HRID 1615769 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH:14]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=2)[NH:13][C:12](=[O:24])[C@H:11]1[CH2:25][CH:26]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[CH2:34][C:35]([O:37][CH3:38])=[O:36].O>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH:14]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=2)[N:13]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[C:12](=[O:24])[C@H:11]1[CH2:25][CH:26]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 68154355HCID 68154355, compound

Product 1

HCID 68154521HCID 68154521, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere 59 mg (1.4 mmol) sodium hydride were added at 0° C. to 0.50 g (1.2 mmol) (2R)-tert-butyl-2-(cycloheptylmethyl)-5-(3,5-difluorophenyl)-3-oxopiperazine-1-carboxylate (isomer 3.1) in 20 ml DMF. After 20 min at 0° C. 0.13 ml (1.4 mmol) methyl bromoacetate were added and the mixture was stirred for 30 min at 0° C. Then the reaction mixture was stirred for 5 h at RT. The reaction mixture was mixed with water and extracted twice with ethyl acetate. The combined organic phases were dried and evaporated down.

Workup

  1. stirringThen the reaction mixture was stirred for 5 h at RT
  2. extractionextracted twice with ethyl acetate
  3. customThe combined organic phases were dried
  4. customevaporated down

Sources & evidence

ORD record
ord-419c2d7d8bf74160adeadbec70d7a7c5
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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