tert-butyl 2-[(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]acetate → 2-[(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

HRID 11005Notes

Reaction equation

HRID 11005 reaction equation
C([O:5][C:6](=[O:56])[CH2:7][C@@:8]1([CH3:55])[C:12]2=[N:13][CH:14]=[C:15]([N:18]([CH2:29][CH:30]=[CH2:31])[C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[C:16](=[O:17])[N:11]2[C@@H:10]([C:32](=[O:54])[NH:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([NH:43][C:44]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:45])=[NH:42])=[CH:37][CH:36]=2)[CH2:9]1)(C)(C)C>O1CCOCC1.Cl>[CH2:29]([N:18]([C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[C:15]1[C:16](=[O:17])[N:11]2[C@@H:10]([C:32](=[O:54])[NH:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([C:41]([NH:43][C:44]([O:46][CH2:47][C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)=[O:45])=[NH:42])=[CH:37][CH:36]=3)[CH2:9][C@:8]([CH2:7][C:6]([OH:56])=[O:5])([CH3:55])[C:12]2=[N:13][CH:14]=1)[CH:30]=[CH2:31]

Participants

3

Reactant 1

HCID 145857205tert-butyl 2-[(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]acetate

Product 1

HCID 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 acidYield 102%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of intermediate 38d (262.3 mg, 0.34 mmol) in 5 mL 4M HCl dioxane was stirred at rt for 2 h. The solvent was removed in vacuo, then the compound was triturated with ether to afford 245 mg (100%) of intermediate 39a. MS (ESI) 707.4 (M+H+), 705.3 (M−H+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe compound was triturated with ether

Sources & evidence

ORD record
ord-060cc32606934662a50b466e7bc01a34
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Reaction notes

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