(S)-2-amino-3-(4-tert-butoxyphenyl)-N-((S)-1,1-diethoxypropan-2-yl)-N-(quinolin-8-ylmethyl)propanamide → 2-allyl-2-(2-((S)-3-(4-tert-butoxyphenyl)-1-(((S)-1,1-diethoxypropan-2-yl)(quinolin-8-ylmethyl)amino)-1-oxopropan-2-ylamino)-2-oxoethyl)-N-((R)-1-phenylethyl)hydrazinecarboxamide

HRID 718934Notes

Reaction equation

HRID 718934 reaction equation
[CH2:1]([N:4]([CH2:17][C:18]([OH:20])=O)[NH:5][C:6](=[O:16])[NH:7][C@@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])[CH:2]=[CH2:3].[NH2:21][C@@H:22]([CH2:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[CH:49][CH:48]=1)[C:23]([N:25]([C@@H:37]([CH3:45])[CH:38]([O:42][CH2:43][CH3:44])[O:39][CH2:40][CH3:41])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:36]=1[N:35]=[CH:34][CH:33]=[CH:32]2)=[O:24]>>[CH2:1]([N:4]([CH2:17][C:18]([NH:21][C@@H:22]([CH2:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[CH:49][CH:48]=1)[C:23]([N:25]([C@@H:37]([CH3:45])[CH:38]([O:39][CH2:40][CH3:41])[O:42][CH2:43][CH3:44])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:36]=1[N:35]=[CH:34][CH:33]=[CH:32]2)=[O:24])=[O:20])[NH:5][C:6]([NH:7][C@@H:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:9])=[O:16])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 67075208(S)-2-amino-3-(4-tert-butoxyphenyl)-N-((S)-1,1-diethoxypropan-2-yl)-N-(quinolin-8-ylmethyl)propanamideHCID 67075317(R)-2-(1-allyl-2-(1-phenylethylcarbamoyl)hydrazinyl)acetic acid

Product 1

HCID 670753632-allyl-2-(2-((S)-3-(4-tert-butoxyphenyl)-1-(((S)-1,1-diethoxypropan-2-yl)(quinolin-8-ylmethyl)amino)-1-oxopropan-2-ylamino)-2-oxoethyl)-N-((R)-1-phenylethyl)hydrazinecarboxamideYield 85.1%

Procedure

According to the procedure described in the synthesis method of Compound II-1, (R)-2-(1-allyl-2-(1-phenylethylcarbamoyl)hydrazinyl)acetic acid (Compound VI-4) 133 mg (0.48 mmol) was coupled with (S)-2-amino-3-(4-tert-butoxyphenyl)-N—((S)-1,1-diethoxy-propan-2-yl)-N-(quinolin-8-ylmethyl)propanamide (Compound IV-3) 203 mg (0.4 mmol) and purified on silica gel column chromatography (n-hexane:Ethyl acetate=90:10 to 80:20) to obtain the title compound 261 mg (85%).

Workup

  1. custompurified on silica gel column chromatography (n-hexane:Ethyl acetate=90:10 to 80:20)

Sources & evidence

ORD record
ord-a60354c5e0e7424f86d43c4059550e97
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

Loading…