Water → HCID 68213456, compound

HRID 1186250Notes

Reaction equation

HRID 1186250 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([N:12]([CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:8][CH2:7]2.[C:32]([C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1)([CH3:35])([CH3:34])[CH3:33].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[C:32]([C:36]1[CH:37]=[CH:38][C:39]([CH2:40][O:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[CH2:10][CH:9]([N:12]([CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:8][CH2:7]3)=[CH:42][CH:43]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 68213447HCID 68213447, compound

Product 1

HCID 68213456HCID 68213456, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

550 mg (1.29 mmol) of the compound from Example 3A were dissolved in 35 ml of DMF, 320 μl (1.6 mmol) of 4-tert-butylbenzyl bromide and 1.4 g (4.14 mmol) of cesium carbonate were added and the mixture was stirred at RT for 18 h. Water was then added, and the mixture was extracted repeatedly with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The crude product obtained was purified by preparative HPLC (method 1).

Workup

  1. extractionthe mixture was extracted repeatedly with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-be80ecc01fbc467f9f315bc8ffb3511a
Source dataset
uspto-grants-2014_03
Patent number
US08673903B2

Reaction notes

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