Sodium Hydroxide → (S)-2-{3-[2-(6-Hydroxycarbamoyl-hexylcarbamoyl)-1H-indol-5-yl]-propionylamino}-3-phenyl-propionic acid

HRID 548260Notes

Reaction equation

HRID 548260 reaction equation
C1([O:6][C:7](=[O:43])[C@@H:8]([NH:16][C:17](=[O:42])[CH2:18][CH2:19][C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[NH:25][C:24]([C:29](=[O:41])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37](=[O:40])[NH:38][OH:39])=[CH:23]3)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)CCCC1.[OH-].[Na+]>C1COCC1.CO>[OH:39][NH:38][C:37]([CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][NH:30][C:29]([C:24]1[NH:25][C:26]2[C:22]([CH:23]=1)=[CH:21][C:20]([CH2:19][CH2:18][C:17]([NH:16][C@@H:8]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:7]([OH:43])=[O:6])=[O:42])=[CH:28][CH:27]=2)=[O:41])=[O:40]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15940511(S)-2-{3-[2-(6-Hydroxycarbamoyl-hexylcarbamoyl)-1H-indol-5-yl]-propionylamino}-3-phenyl-propionic acid cyclopentyl ester

Product 1

HCID 15940651(S)-2-{3-[2-(6-Hydroxycarbamoyl-hexylcarbamoyl)-1H-indol-5-yl]-propionylamino}-3-phenyl-propionic acidYield 47.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Compound (100) (80 mg, 0.14 mmol) was dissolved in THF/MeOH (1 ml/0.5 ml) and 1.4 M NaOH (0.5 ml) added. The reaction was stirred at room temperature for 2 h. THF was removed by blowing a stream of N2 gas at the surface of the solution and the residual material purified by preparative HPLC to give compound (101) (34.9 mg), LCMS purity 95%, m/z 523 [M++H]+, 1H NMR (400 MHz, MeOD), δ: 1.35-1.50 (4H, m, alkyl), 1.60-1.75 (4H, m, alkyl), 2.15 (2H, br t, CH2), 2.55 (2H, br t, CH2), 2.95 (3 H, m, CH+CH2), 3.10 (1H, dd, CH), 4.65, (1H, m, NHCHCO), 7.00-7.15 (7H, m, Ar), 7.35-7.41 (2H, m, Ar)

Workup

  1. customTHF was removed
  2. customthe residual material purified by preparative HPLC

Sources & evidence

ORD record
ord-543a5a28ffc448c98d35d9def4359b5a
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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