Potassium Carbonate → HCID 58787790, compound

HRID 1375709Notes

Reaction equation

HRID 1375709 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([O:12][CH2:13]/[C:14](/[C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1)=[C:15](/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)\[C:16]([OH:18])=[O:17])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]Br.C([O-])([O-])=O.[K+].[K+].[Cl-].[NH4+]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([O:12][CH2:13]/[C:14](/[C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1)=[C:15](/[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)\[C:16]([O:18][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][Br:35])=[O:17])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 25517Ammonium ChlorideHCID 58787785HCID 58787785, compound

Product 1

HCID 58787790HCID 58787790, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.88 g of (2Z)-4-{[N-(tert-butoxycarbonyl)glycyl]oxy}-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid and 9.6 g of 1,6-dibromohexane in 20 mL of DMF was stirred at rt with 550 mg of K2CO3 for 2 h. Then saturated ammonium chloride solution was added and extracted with EtOAc. The organic layer was combined and washed with brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by flash chromatography over silica gel (5–50% EtOAc/hexane) to afford 2.1 g of the titled compound as a colorless oil. 1H NMR (500 MHz, acetone-d6): δ 7.76 (d, 2H), 7.43 (d, 2H), 7.17 (m, 3H), 7.08 (d, 2H), 6.24 (br s, NH), 5.27 (s, 2H), 4.24 (t, 2H), 3.68 (d, 2H), 3.45 (t, 2H), 3.05 (s, 3H), 1.81 (m, 2H), 1.68 (m, 2H), 1.44–1.32 (m, 4H), 1.39 (s, 9H).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated
  5. customthe residue was purified by flash chromatography over silica gel (5–50% EtOAc/hexane)

Sources & evidence

ORD record
ord-8daeed3557f34d5caca0e173a0736765
Source dataset
uspto-grants-2007_01
Patent number
US07169809B2

Reaction notes

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