(S)-8,8-diallyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid → benzyl N-[(6S)-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-8,8-bis(prop-2-enyl)-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamate

HRID 10993Notes

Reaction equation

[CH2:1]([N:4]([C:15]1[C:20](=[O:21])[N:19]2[C@H:22]([C:28](=[O:50])[NH:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([C:37]([NH:39][C:40]([O:42][CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[O:41])=[NH:38])=[CH:33][CH:32]=3)[CH2:23][C@@H:24]([CH2:25][CH:26]=[CH2:27])[C:18]2=[N:17][CH:16]=1)[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3].[CH2:51]([C:54]1(CC=C)C2=NC=C(N(CC=C)C(OCC3C=CC=CC=3)=O)C(=O)N2[C@H](C(O)=O)C1)[CH:52]=C.Cl.C(OC(=O)NC(C1C=CC(CN)=CC=1)=N)C1C=CC=CC=1>>[CH2:1]([N:4]([C:15]1[C:20](=[O:21])[N:19]2[C@H:22]([C:28](=[O:50])[NH:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]([C:37]([NH:39][C:40]([O:42][CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[O:41])=[NH:38])=[CH:35][CH:36]=3)[CH2:23][C:24]([CH2:54][CH:51]=[CH2:52])([CH2:25][CH:26]=[CH2:27])[C:18]2=[N:17][CH:16]=1)[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH:2]=[CH2:3]

Participants

Reactant 3

HCID 57444829(S)-8,8-diallyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid

HCID 145832047Benzyl ((4-(aminomethyl)phenyl)(imino)methyl)carbamate hydrochloride

HCID 145857219benzyl N-[(6S,8R)-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-8-prop-2-enyl-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamate

Product 1

HCID 145857218benzyl N-[(6S)-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-8,8-bis(prop-2-enyl)-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamateYield 41%

Procedure

According to the procedure for the preparation of 28e, 29d (162 mg, 0.360 mmol) was coupled with [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester hydrochloride to afford after flash chromatography (66% EtOAc/hexanes) 105 mg (41%) of 29e. MS (ESI) 715.5 (M+H+), 737.5 (M+Na+).

Sources & evidence

ORD record: ord-4f9a90965b4c40a7adc1535c3ce407ad
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094783B2

Reaction notes

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