Aniline → benzyl N-[(6R,8S)-8-(2-anilino-2-oxoethyl)-8-methyl-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamate

HRID 11006Notes

Reaction equation

HRID 11006 reaction equation
[CH2:1]([N:4]([C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44])[C:5]1[C:10](=[O:11])[N:9]2[C@@H:12]([C:20](=[O:42])[NH:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([NH:31][C:32]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:33])=[NH:30])=[CH:25][CH:24]=3)[CH2:13][C@:14]([CH2:16][C:17]([OH:19])=O)([CH3:15])[C:8]2=[N:7][CH:6]=1)[CH:2]=[CH2:3].[NH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>>[CH2:46]([O:45][C:43](=[O:44])[N:4]([CH2:1][CH:2]=[CH2:3])[C:5]1[C:10](=[O:11])[N:9]2[C@@H:12]([C:20](=[O:42])[NH:21][CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]([NH:31][C:32]([O:34][CH2:35][C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)=[O:33])=[NH:30])=[CH:27][CH:28]=3)[CH2:13][C@@:14]([CH3:15])([CH2:16][C:17](=[O:19])[NH:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[C:8]2=[N:7][CH:6]=1)[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 1458572152-[(6R,8S)-8-methyl-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-3-[phenylmethoxycarbonyl(prop-2-enyl)amino]-6,7-dihydropyrrolo[1,2-a]pyrimidin-8-yl]acetic acid

Product 1

HCID 145857211benzyl N-[(6R,8S)-8-(2-anilino-2-oxoethyl)-8-methyl-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamateYield 57%

Procedure

Following a procedure similar to that for the preparation of intermediate 18 g, intermediate 39a (20 mg, 0.028 mmol) was coupled with aniline (3.39 mg, 0.036 mmol) to provide 12.4 mg (57%) of intermediate 40a. MS (ESI) 782.3 (M+H+).

Sources & evidence

ORD record
ord-002a8eb87a59427d8655a91589e79e04
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Reaction notes

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