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)-1,4-dioxo-4-(tritylamino)butan-2-ylamino)-2-oxoethoxy)urea

HRID 719026Notes

Reaction equation

HRID 719026 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]([NH:45][C:46]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44])[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](=[O:44])[NH:45][C:46]([C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=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:25][CH2:26][CH3:27])[O:28][CH2:29][CH3:30])=[O:21])=[O:14])=[O:15])=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 533975002-(3-(4-Chlorobenzyl)ureidooxy)acetic acidHCID 67075021(S)-2-amino-N1-(benzo[b]thiophen-3-ylmethyl)-N1-((S)-1,1-diethoxy-propan-2-yl)-N4-tritylsuccinamide

Product 1

HCID 866526211-(4-chlorobenzyl)-3-(2-((S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxy-propan-2-yl)amino)-1,4-dioxo-4-(tritylamino)butan-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) 60 mg (0.23 mmol) was coupled with (S)-2-amino-N1-(benzo[b]thiophen-3-ylmethyl)-N1—((S)-1,1-diethoxypropan-2-yl)-N4-tritylsuccinamide (Compound IV-21) 100 mg (0.15 mmol) to obtain the title compound.

Sources & evidence

ORD record
ord-72cf942ac5ce485ba2427ca5f9f6cb7c
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

Loading…