Dimethylformamide → HCID 86624064, compound

HRID 548209Notes

Reaction equation

HRID 548209 reaction equation
Cl.[F:2][C:3]([F:35])([F:34])[C:4]1[CH:5]=[C:6]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:7][O:8][CH2:9][CH:10]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:11][NH:12][C:13]([CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[O:14].Br[CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:35][C:3]([F:34])([F:2])[C:4]1[CH:5]=[C:6]([CH:27]=[C:28]([C:30]([F:32])([F:33])[F:31])[CH:29]=1)[CH2:7][O:8][CH2:9][CH:10]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:11][NH:12][C:13]([CH:15]1[CH2:20][CH2:19][N:18]([CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:17][CH2:16]1)=[O:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 86624065HCID 86624065, compound

Product 1

HCID 86624064HCID 86624064, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Compound 4 produced in Example 32 (1.26 g, 2.4 mmol), tert-butyl bromoacetate (0.38 mL, 2.6 mmol), potassium carbonate (1.00 g, 7.2 mmol) and DMF (10 mL) was stirred for 20 hours at room temperature. Water was added to the reaction mixture followed by extracting with ethyl acetate. The organic layers were combined, washed with water and a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was evaporated therefrom in vacuo to give Compound 79 (1.34 g, 93%).

Workup

  1. extractionby extracting with ethyl acetate
  2. washwashed with water
  3. dry with materiala saturated saline solution and dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-294179ecc67b4bf4987047a0b53dc270
Source dataset
uspto-grants-2011_05
Patent number
US07939552B2

Reaction notes

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