2-(2-((4-Chlorobenzyl)carbamoyl)-1-methylhydrazinyl)acetic acid → 4-(4-chlorobenzyl)-1-(2-((S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1,4-dioxo-4-(tritylamino)butan-2-ylamino)-2-oxoethyl)-1-methylsemicarbazide

HRID 718992Notes

Reaction equation

HRID 718992 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]([CH2:43][C:44]([NH:46][C:47]([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[C:21]([N:23]([CH2:33][C:34]1[C:35]2[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=2[S:37][CH:38]=1)[C@@H:24]([CH3:32])[CH:25]([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])=[O:22]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8](=[O:9])[NH:10][N:11]([CH2:13][C:14]([NH:19][C@@H:20]([CH2:43][C:44](=[O:45])[NH:46][C:47]([C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[C:21]([N:23]([CH2:33][C:34]2[C:35]3[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=3[S:37][CH:38]=2)[C@@H:24]([CH3:32])[CH:25]([O:26][CH2:27][CH3:28])[O:29][CH2:30][CH3:31])=[O:22])=[O:16])[CH3:12])=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 533975012-(2-((4-Chlorobenzyl)carbamoyl)-1-methylhydrazinyl)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 866525874-(4-chlorobenzyl)-1-(2-((S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1,4-dioxo-4-(tritylamino)butan-2-ylamino)-2-oxoethyl)-1-methylsemicarbazide

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) 63 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-27854d68aa574f739b2e63e7e553a340
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

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