Water → HCID 6709790, compound

HRID 1008245Notes

Reaction equation

HRID 1008245 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@@H:4]([NH:13][C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:27](Br)[CH:28]=[CH2:29].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]([NH:13][C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:29][CH:28]=[CH2:27])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 6709788HCID 6709788, compound

Product 1

HCID 6709790HCID 6709790, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 18 (30 g, 107.4 mmol, 1.0 equiv) in DMF (170 mL) at room temperature was added solid K2CO3 (29.6 g, 214.2 mmol, 2.0 equiv) then allylbromide (10.2 mL, 116.3 mmol, 1.1 equiv) dropwise. The suspension was stirred at room temperature for 9 hours, after which time water (500 mL) was added and extracted with ether (4×250 mL). The organics were combined, washed with brine, dried over MgSO4, and concentrated. Purification by flash chromatography (20→60% EtOAc/hexane) afforded 19 (31.6 g, 92%) as a clear oil. Rf=0.27 (25% EtOAc/hexane); FTIR (neat, cm−1) 3343, 2919, 1721, 1510, 1239, 1215, 1176, 1052, 1017; 1H NMR (400 MHz, CDCl3) δ7.00 (d, J=8.4 Hz, 2H), 6.79 (d, J=8.8 Hz, 2H), 5.99 (m, 1H), 5.85 (m, 1H), 5.44 (d, J=8.0 Hz, 1H), 5.36 (dd, J=17.4, 1.2 Hz, 1H), 5.25 (s, 1H), 5.22 (dd, J=10.2, 1.6 Hz, 1H), 5.15 (dd, J=10.4, 1.2 Hz, 1H), 4.56 (dd, J=14.2, 6.0 Hz, 1H), 4.51 (d, J=5.6 Hz, 2H), 4.45 (d, J=5.2 Hz, 2H), 3.66 (s, 3H), 3.03 (dd, J=14.4, 5.2 Hz, 1H), 2.96 (dd, J=14.0, 6.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ172.0, 157.5, 155.4, 133.1, 132.5, 130.0, 127.8, 117.4, 117.3, 114.5, 68.4, 65.5, 54.7, 52.0, 37.0; MS (ES+) calculated for C17H21NO5 (M+H)+: 320.1420, found: 320.2.

Workup

  1. extractionextracted with ether (4×250 mL)
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification by flash chromatography (20→60% EtOAc/hexane)

Sources & evidence

ORD record
ord-efeaf9d349a746dca02e81d80880f313
Source dataset
uspto-grants-2004_09
Patent number
US06797819B1

Reaction notes

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