Ethyl bromoacetate → HCID 178472989, compound

HRID 272231Notes

Reaction equation

HRID 272231 reaction equation
[CH2:1]([N:8]([C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([N:8]([C:9]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:15])[C@H:16]1[CH2:17][CH2:18][C@H:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:24][CH:23]=2)[CH2:20][CH2:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 178453042HCID 178453042, compound

Product 1

HCID 178472989HCID 178472989, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3.82 g (10 mmol) of tert-butyl trans-benzyl[4-(4-hydroxyphenyl)-cyclohexyl]carbamate (cf. preparation 1.2) and of 0.48 g of 60% sodium hydride (12 mmol) in dimethylformamide (38 ml) is stirred for 25 minutes and then 1.44 ml of ethyl bromoacetate (13 mmol) are added. The reaction is left stirring for 4 h. The reaction medium is neutralized by the addition of a saturated aqueous ammonium chloride solution. The solvents are evaporated under reduced pressure and water and dichloromethane are added. The organic phase is washed 5 times with water and then dried over magnesium sulfate. Ethyl trans-(4-{4-[benzyl(tert-butoxycarbonyl)amino]cyclohexyl}phenoxy)acetate is obtained in the form of a white solid (4.68 g, 100%) after evaporation of the solvents under reduced pressure.

Workup

  1. waitThe reaction is left
  2. customThe solvents are evaporated under reduced pressure and water and dichloromethane
  3. additionare added
  4. washThe organic phase is washed 5 times with water
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-649ff54ecbc14f8594d80e06c1acc13e
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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