2-(2-((4-Chlorobenzyl)carbamoyl)-1-methylhydrazinyl)acetic acid → (S)-tert-butyl 4-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-3-(2-(2-(4-chlorobenzylcarbamoyl)-1-methylhydrazinyl)acetamido)-4-oxobutanoate

HRID 1254576Notes

Reaction equation

HRID 1254576 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]([NH:10][N:11]([CH2:13][C:14]([OH:16])=O)[CH3:12])=[O:9])=[CH:4][CH:3]=1.[NH2:19][C@H:20]([C:29]([N:31]([CH2:41][C:42]1[C:43]2[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=2[S:45][CH:46]=1)[C@@H:32]([CH3:40])[CH:33]([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36])=[O:30])[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>>[S:45]1[CH:46]=[C:42]([CH2:41][N:31]([C@@H:32]([CH3:40])[CH:33]([O:34][CH2:35][CH3:36])[O:37][CH2:38][CH3:39])[C:29](=[O:30])[C@@H:20]([NH:19][C:14](=[O:16])[CH2:13][N:11]([CH3:12])[NH:10][C:8](=[O:9])[NH:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:18][CH:17]=2)[CH2:21][C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[C:43]2[CH:50]=[CH:49][CH:48]=[CH:47][C:44]1=2

Participants

3

Reactant 2

HCID 533975012-(2-((4-Chlorobenzyl)carbamoyl)-1-methylhydrazinyl)acetic acidHCID 67075220(S)-tert-butyl 3-amino-4-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-4-oxobutanoate

Product 1

HCID 67088509(S)-tert-butyl 4-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-3-(2-(2-(4-chlorobenzylcarbamoyl)-1-methylhydrazinyl)acetamido)-4-oxobutanoate

Procedure

According to the procedure described in the synthesis method of Compound II-15, 2-(2-(4-chlorobenzylcarbamoyl)-1-methylhydrazinyl)acetic acid (Compound VI-7) 88 mg (0.32 mmol) was coupled with (S)-tert-butyl 3-amino-4-((benzo[b]thiophen-3-ylmethyl)-((S)-1,1-diethoxypropan-2-yl)amino)-4-oxobutanoate IV-18) 100 mg (0.22 mmol) to obtain the title compound.

Sources & evidence

ORD record
ord-51b8986210d340b0b19905f439398b08
Source dataset
uspto-grants-2013_06
Patent number
US08455488B2

Reaction notes

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