Tetrahydrofuran → HCID 69418695, compound

HRID 852855Notes

Reaction equation

HRID 852855 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][CH2:5][CH:6]([NH:26][C:27](=[O:40])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:9]=1.[OH-].[K+].C1COCC1>CO.O>[C:34]1([CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][C:27]([NH:26][C@H:6]([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:9]=2)[CH2:5][CH2:4][C:3]([OH:41])=[O:2])=[O:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 69413727HCID 69413727, compound

Product 1

HCID 69418695HCID 69418695, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-(7-phenyl-heptanoylamino)-5-[1-(3-phenyl-propyl)-1H-indol-3-yl]-pentanoic acid methyl ester (95 mg, 0.172 mmol) in MeOH (0.5 mL) was added KOH (100 mg, 1.79 mmol) in water (0.5 mL). THF (1 mL) was added to homogenise the solution and the reaction was complete in 40 minutes. The solvents were removed and water added. Upon washing with ether the aqueous layer was acidified with aqueous HCl and the resultant precipitate filtered. Upon drying the solid was recrystallised from THF/Et2O to afford the title compound (70 mg, 76%), mp 100-101.5° C. 1H NMR (DMSO-d6) δ 7.64-7.59 (2H, m), 7.35-7.08 (12H, m), 7.03-6.98 (1H, m), 4.10 (2H, t, J=6.59 Hz), 4.04 (1H, br s), 2.84 (1H, dd, J=6.65, 14.39 Hz), 2.78 (1H, dd, J=6.45, 14.39 Hz), 2.55-2.49 (4H, m), 2.34-2.12 (2H, m), 2.05-2.00 (4H, m), 1.86-1.75 (1H, m), 1.66-1.44 (5H, m), 1.21 (4H, m), 13C NMR (DMSO-d6) □ 174.4, 171.9, 142.3, 141.3, 135.9, 128.3, 128.2, 128.0, 126.5, 125.8, 125.5, 120.9, 118.9, 118.3, 117.9, 110.9, 109.5, 35.6, 35.1, 32.4, 31.5, 30.9, 30.7, 30.5, 29.2, 28.5, 28. 5, 25.3. ISMS: 539 (M+H).

Workup

  1. customThe solvents were removed
  2. additionwater added
  3. washUpon washing with ether the aqueous layer
  4. filtrationthe resultant precipitate filtered
  5. customUpon drying the solid
  6. customwas recrystallised from THF/Et2O

Sources & evidence

ORD record
ord-623519aa9d6049e28c2fea95c624481d
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

Loading…