2-(2-(Ethylcarbamoyl)-1-methylhydrazinyl)acetic acid → 1-(2-((S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-3-(4-tert-butoxyphenyl)-1-oxopropan-2-ylamino)-2-oxoethyl)-4-ethyl-1-methylsemicarbazide

HRID 718983Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][N:7]([CH2:9][C:10]([OH:12])=O)[CH3:8])=[O:5])[CH3:2].[NH2:13][C@@H:14]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[CH:40][CH:39]=1)[C:15]([N:17]([CH2:27][C:28]1[C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[S:31][CH:32]=1)[C@@H:18]([CH3:26])[CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[O:16]>>[S:31]1[CH:32]=[C:28]([CH2:27][N:17]([C@@H:18]([CH3:26])[CH:19]([O:20][CH2:21][CH3:22])[O:23][CH2:24][CH3:25])[C:15](=[O:16])[C@@H:14]([NH:13][C:10](=[O:12])[CH2:9][N:7]([CH3:8])[NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])[CH2:37][C:38]2[CH:39]=[CH:40][C:41]([O:44][C:45]([CH3:46])([CH3:48])[CH3:47])=[CH:42][CH:43]=2)[C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]1=2

Participants

Reactant 2

HCID 533974172-(2-(Ethylcarbamoyl)-1-methylhydrazinyl)acetic acid

HCID 67075252(S)-2-amino-N-(benzo[b]thiophen-3-ylmethyl)-3-(4-tert-butoxyphenyl)-N-((S)-1,1-diethoxypropan-2-yl)propanamide

Product 1

HCID 670750241-(2-((S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-3-(4-tert-butoxyphenyl)-1-oxopropan-2-ylamino)-2-oxoethyl)-4-ethyl-1-methylsemicarbazide

Procedure

According to the procedure described in the synthesis method of Compound II-15, 2-(2-(ethylcarbamoyl)-1-methylhydrazinyl)acetic acid (Compound VI-9) 51 mg (0.29 mmol) was coupled with (S)-2-amino-N-(benzo[b]thiophen-3-ylmethyl)-3-(4-tert-butoxyphenyl)-N—((S)-1,1-diethoxypropan-2-yl)propanamide (Compound IV-6) 100 mg (0.20 mmol) to obtain the title compound.

Sources & evidence

ORD record: ord-38c61c018a43480394a4ef23c4cecd34
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193734B2

Reaction notes

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