Tetrahydrofuran → (S)-5-(1-Benzyl-1H-indol-3-yl)-4-(7-phenyl-heptanoylamino)-pentanoic acid

HRID 852854Notes

Reaction equation

HRID 852854 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][CH2:5][CH:6]([NH:24][C:25](=[O:38])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:9]=1.[OH-].[K+].C1COCC1>CO.O>[CH2:17]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH2:7][C@@H:6]([NH:24][C:25](=[O:38])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:5][CH2:4][C:3]([OH:39])=[O:2])=[CH:9]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 694147775-(1-benzyl-1H-indol-3-yl)-4-(7-phenyl-heptanoylamino)-pentanoic acid methyl ester

Product 1

HCID 69413168(S)-5-(1-Benzyl-1H-indol-3-yl)-4-(7-phenyl-heptanoylamino)-pentanoic acidYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-(1-benzyl-1H-indol-3-yl)-4-(7-phenyl-heptanoylamino)-pentanoic acid methyl ester (48 mg, 0.092 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 min. The solvents were removed and water added. Upon washing with Et2O 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 (30 mg, 64%), mp 130.4-131.9° C. 13C NMR (DMSO-d6) δ 174.3, 171.8, 142.3, 138.4, 135.9, 128.4, 128.2, 128.2, 127.2, 127.1, 126.8, 125.5, 121.1, 118.9, 118.5, 111.3, 109.9, 48.9, 48.6, 35.5, 35.1, 30.9, 30.7, 30.5, 29.1, 28.5, 28.4, 25.2. ISMS: 511 (M+H).

Workup

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

Sources & evidence

ORD record
ord-5824c6a20604473398c29e7284dfc824
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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