[(methoxy{[(3S,3aS,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl]oxy}phosphoryl)oxy]methyl 2-butyl-4-chloro-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate → HCID 178441709, compound

HRID 384581Notes

Reaction equation

[CH2:1]([C:5]1[N:6]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[C:46]3[N:50](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:49]=[N:48][N:47]=3)=[CH:36][CH:35]=2)[C:7]([C:11]([O:13][CH2:14][O:15][P:16]([O:31][CH3:32])([O:18][C@H:19]2[CH2:23][O:22][C@@H:21]3[C@H:24]([O:27][N+:28]([O-:30])=[O:29])[CH2:25][O:26][C@H:20]23)=[O:17])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]>CO>[CH2:1]([C:5]1[N:6]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[C:46]3[NH:50][N:49]=[N:48][N:47]=3)=[CH:36][CH:35]=2)[C:7]([C:11]([O:13][CH2:14][O:15][P:16]([O:31][CH3:32])([O:18][C@H:19]2[CH2:23][O:22][C@@H:21]3[C@H:24]([O:27][N+:28]([O-:30])=[O:29])[CH2:25][O:26][C@H:20]23)=[O:17])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

Each diastereomer of [(methoxy{[(3S,3aS,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl]oxy}phosphoryl)oxy]methyl 2-butyl-4-chloro-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate was dissolved in methanol and heated to 70° C. for 2 hours. The residue was purified by HPLC reverse phase (C-18), eluting with acetonitrile/water+0.1% trifluoroacetic acid to give the title compound.

Workup

customThe residue was purified by HPLC reverse phase (C-18)
washeluting with acetonitrile/water+0.1% trifluoroacetic acid

Sources & evidence

ORD record: ord-dc2493456b544c7c8d61ecd2f22c91d7
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367711B2

Reaction notes

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