(3R)-ethyl 3-(2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxyethyl)-3,5-dimethylphenyl)acetamido)-3-(3-nitrophenyl)propanoate → (3R)-ethyl 3-(3-aminophenyl)-3-(2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxyethyl)-3,5-dimethylphenyl)acetamido)propanoate

HRID 735628Notes

Reaction equation

HRID 735628 reaction equation
[C:1]([O:5][C:6]([N:8]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][CH:20]([C:40]3[CH:45]=[C:44]([CH3:46])[C:43]([CH2:47][CH2:48][OH:49])=[C:42]([CH3:50])[CH:41]=3)[C:21]([NH:23][C@@H:24]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-])=O)[CH:32]=3)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:37][C:33]1[CH:32]=[C:31]([C@H:24]([NH:23][C:21](=[O:22])[CH:20]([NH:19][C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[C:9]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:51]([O:53][C:54]([CH3:56])([CH3:57])[CH3:55])=[O:52])=[N:10][CH:11]=[CH:12]3)[C:40]2[CH:45]=[C:44]([CH3:46])[C:43]([CH2:47][CH2:48][OH:49])=[C:42]([CH3:50])[CH:41]=2)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 1

HCID 57842695(3R)-ethyl 3-(2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxyethyl)-3,5-dimethylphenyl)acetamido)-3-(3-nitrophenyl)propanoate

Product 1

HCID 57842620(3R)-ethyl 3-(3-aminophenyl)-3-(2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxyethyl)-3,5-dimethylphenyl)acetamido)propanoateYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 50D (580 mg, 0.74 mmol) in MeOH (30 mL) with Pd/C (35 mg) was stirred under H2 (50 psi) for 2 h. The reaction mixture was filtered and concentrated in vacuo. The crude solid was purified by flash chromatography (0% to 20% MeOH in CH2Cl2) to afford 50E (400 mg, 72%) as a yellow solid. MS (ESI) m/z 756.6 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe crude solid was purified by flash chromatography (0% to 20% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a1872872e5ba4095a876d8240a0972a8
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…