2-(3-(4-Chlorobenzyl)ureidooxy)acetic acid → 1-(4-chlorobenzyl)-3-(2-((S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxy-propan-2-yl)amino)-3-(4-tert-butoxyphenyl)-1-oxopropan-2-ylamino)-2-oxoethoxy)urea

HRID 719021Notes

Reaction equation

HRID 719021 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][NH:7][C:8](=[O:15])[NH:9][O:10][CH2:11][C:12]([OH:14])=O)=[CH:4][CH:3]=1.[NH2:18][C@@H:19]([CH2:42][C:43]1[CH:48]=[CH:47][C:46]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[CH:45][CH:44]=1)[C:20]([N:22]([CH2:32][C:33]1[C:34]2[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=2[S:36][CH:37]=1)[C@@H:23]([CH3:31])[CH:24]([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])=[O:21]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([NH:9][O:10][CH2:11][C:12]([NH:18][C@@H:19]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([O:49][C:50]([CH3:53])([CH3:51])[CH3:52])=[CH:45][CH:44]=2)[C:20]([N:22]([CH2:32][C:33]2[C:34]3[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=3[S:36][CH:37]=2)[C@@H:23]([CH3:31])[CH:24]([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])=[O:21])=[O:14])=[O:15])=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 533975002-(3-(4-Chlorobenzyl)ureidooxy)acetic acidHCID 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 866526171-(4-chlorobenzyl)-3-(2-((S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxy-propan-2-yl)amino)-3-(4-tert-butoxyphenyl)-1-oxopropan-2-ylamino)-2-oxoethoxy)urea

Procedure

According to the procedure described in the synthesis method of Compound II-15, 2-(3-(4-chlorobenzyl)ureidooxy)acetic acid (Compound VI-11) 76 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-2b27ea7769764a9491cfec42cbc3b8af
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

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