Potassium Carbonate → HCID 69413201, compound

HRID 852888Notes

Reaction equation

HRID 852888 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][CH:6]([NH:15][C:16](=[O:29])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Cl.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38]Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][CH:6]([NH:15][C:16](=[O:29])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:38][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 69415564HCID 69415564, compound

Product 1

HCID 69413201HCID 69413201, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(RS)-5-(4-Hydroxy-phenyl)-4-(7-phenyl-heptanoylamino)-pentanoic acid methyl ester 92 (889 mg, 2.16 mmol), 2-picolylchloride hydrochloride (570 mg, 3.47 mmol) and finely powdered anhydrous K2CO3 (1.45 g, 10.5 mmol) was stirred in dry DMF (7 mL) for 48 hr. The mixture was poured onto water (40 mL) and extracted into EtOAc. The extract was successively washed with HCl solution (1 M, 30 mL), saturated NaHCO3 solution, brine, and then dried with MgSO4. Concentration of the solvent in vacuo afforded 93 (747 mg, 69 %): 1H NMR (CDCl3) δ 1.15-1.40 (m, 4H); 1.40-1.70 (m, 5H); 1.73-1.85 (m, 1H); 2.08 (t, J=7.6 Hz, 2H); 2.34 (m, 2H); 2.58 (t, J=7.6 Hz, 2H); 2.69 (dd, J=15, 6.9 Hz, 1H); 2.77 (dd, J=15, 6.2 Hz, 1H); 3.64 (s, 3H); 4.06-4.21 (m, 1H); 5.17 (s, 2H); 5.37 (d, J=9.3 Hz, 1H); 6.91 (d, J=8.4 Hz, 2H); 7.10 (d, J=8.4 Hz, 2H); 7.12-7.31 (m, 6H); 7.51 (d, J=7.5 Hz, 1H); 7.71 (dt, J=7.5, 1.6 Hz, 1H); 8.60 (m, J=6.0 Hz, 1H). 13C NMR (CDCl3) δ 174.4, 173.0, 157.5, 157.3, 149.4, 142.8, 137.0, 130.3, 125.8, 122.8, 121.5, 130.6, 128.5, 128.4, 115.0, 70.8, 51.9, 50.2, 40.6, 37.0, 36.0, 31.4, 31.1, 29.2, 29.1, 29.0, 25.8. ESMS 503 (M+H)+.

Workup

  1. additionThe mixture was poured onto water (40 mL)
  2. extractionextracted into EtOAc
  3. washThe extract was successively washed with HCl solution (1 M, 30 mL), saturated NaHCO3 solution, brine
  4. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-81eb0de89e15452b86b9b38062801f54
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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