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

HRID 11007Notes

Reaction equation

HRID 11007 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](O)=[O:18])([CH3:15])[C:8]2=[N:7][CH:6]=1)[CH:2]=[CH2:3].[NH:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]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:18])[N:53]3[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]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 8082PiperidineHCID 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 145857209benzyl N-[(6R,8S)-8-methyl-4-oxo-8-(2-oxo-2-piperidin-1-ylethyl)-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamateYield 72.5%

Procedure

Following a procedure similar to that for the preparation of intermediate 18 g, intermediate 39a (20 mg, 0.028 mmol) was coupled with piperidine (8.1 mg, 0.14 mmol) to provide 15.7 mg (71%) of intermediate 41a. MS (ESI) 774.5 (M+H+).

Sources & evidence

ORD record
ord-dab4932fb5d1424e8f1c73ce5b065778
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Reaction notes

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