Sulfuric Acid → HCID 178455987, compound

HRID 1873277Notes

Reaction equation

OS(O)(=O)=O.CC([N:15]1[N:19]=[N:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]([NH:52][C:53](=[O:64])[C@H:54]([C@H:60]([CH2:62][CH3:63])[CH3:61])[NH:55][C:56]([O:58][CH3:59])=[O:57])[CH2:28][C@H:29]([OH:51])[C@@H:30]([NH:38][C:39](=[O:50])[C@H:40]([C:46]([CH3:49])([CH3:48])[CH3:47])[NH:41][C:42]([O:44][CH3:45])=[O:43])[CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:22][CH:21]=2)=[N:16]1)(C1C=CC=CC=1)C>>[NH:18]1[C:17]([C:20]2[CH:21]=[CH:22][C:23]([CH2:26][N:27]([NH:52][C:53](=[O:64])[C@H:54]([C@H:60]([CH2:62][CH3:63])[CH3:61])[NH:55][C:56]([O:58][CH3:59])=[O:57])[CH2:28][C@H:29]([OH:51])[C@@H:30]([NH:38][C:39](=[O:50])[C@H:40]([C:46]([CH3:48])([CH3:49])[CH3:47])[NH:41][C:42]([O:44][CH3:45])=[O:43])[CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:24][CH:25]=2)=[N:16][N:15]=[N:19]1

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 4679732,5,6,10,13-Pentaazatetradecanedioic acid, 12-(1,1-dimethylethyl)-8-hydroxy-6-((4-(2-(1-methyl-1-phenylethyl)-2H-tetrazol-5-yl)phenyl)methyl)-3-(1-methylpropyl)-4,11-dioxo-9-(phenylmethyl)-, dimethyl ester,(3S-(3R*(R*),8R*,9R*,12R*))-

Product 1

HCID 178455987HCID 178455987, compound

Procedure

35 ml of an 80% aqueous H2SO4 solution are added to 354 mg (0.435 mmol) of 1-{4-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-phenyl}-4(S)-hydroxy-2-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane, with ice-cooling. After stirring for 75 min, the mixture is worked up analogously to Example 26 to yield the title compound: HPLC20-100 : tRet =12.6; FAB MS (M+H)+ =696.

Workup

temperaturecooling

Sources & evidence

ORD record: ord-e37f6b1a90334aca80874ec600adfbb7
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06110946

Reaction notes

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