2-(4-(2-(3-((S)-1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid → 2-(4-(2-(3-((S)-1-amino-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid

HRID 735596Notes

Reaction equation

HRID 735596 reaction equation
C(OC([NH:11][C@H:12]([C:19]1[CH:20]=[C:21]([NH:25][C:26]([O:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([CH:37]([NH:41][C:42]3[CH:43]=[C:44]4[C:49](=[CH:50][CH:51]=3)[C:48]([N:52]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[N:47][CH:46]=[CH:45]4)[C:38]([OH:40])=[O:39])=[CH:33][C:32]=2[CH3:67])=[O:27])[CH:22]=[CH:23][CH:24]=1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=O)C1C=CC=CC=1>CO.Cl.[Pd]>[NH2:11][C@H:12]([C:19]1[CH:20]=[C:21]([NH:25][C:26]([O:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([CH:37]([NH:41][C:42]3[CH:43]=[C:44]4[C:49](=[CH:50][CH:51]=3)[C:48]([N:52]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[C:60]([O:62][C:63]([CH3:66])([CH3:64])[CH3:65])=[O:61])=[N:47][CH:46]=[CH:45]4)[C:38]([OH:40])=[O:39])=[CH:33][C:32]=2[CH3:67])=[O:27])[CH:22]=[CH:23][CH:24]=1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 1

HCID 578429002-(4-(2-(3-((S)-1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid

Product 1

HCID 578426432-(4-(2-(3-((S)-1-amino-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acidYield 89%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 34F (670 mg, 0.96 mmol) in MeOH (60 mL) and HCl (2.5 mL, 1.0 M aqueous) and Pd/C (60 mg) was stirred under an atmosphere of H2 (60 psi) for 8 h. The solution was filtered and concentrated in vacuo to yield 34G (600 mg, 89%) as a yellow solid. MS (ESI) m/z 786.4 (M+H)+.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-880cd3a03c354a2c90cc36c36d6c8273
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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