Water → HCID 178512855, compound

HRID 1042047Notes

Reaction equation

HRID 1042047 reaction equation
[Cl-].C([O:6][C:7](=[O:94])[CH2:8][C@@H:9]([C:77](=[O:93])[NH:78][C@@H:79]([CH2:87][O:88]C(C)(C)C)[C:80](=[O:86])[O:81]C(C)(C)C)[NH:10][C:11](=[O:76])[CH2:12][NH:13][C:14](=[O:75])[C@H:15]([CH2:51][CH2:52][CH2:53][NH:54][C:55]([NH:57]S(C1C(C)=C(C)C2OC(C)(C)CC=2C=1C)(=O)=O)=[NH:56])[NH:16][C:17](=[O:50])[CH2:18][CH2:19][C:20](=[O:49])[O:21][CH2:22][O:23][C:24]1[CH:29]=[C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[O+:27]=[C:26]2[C:36]([C:39]3[CH:48]=[CH:47][C:42]4[O:43][CH2:44][CH2:45][O:46][C:41]=4[CH:40]=3)=[CH:37][S:38][C:25]=12)(C)(C)C.O.C([SiH](C(C)C)C(C)C)(C)C.[F:106][C:107]([F:112])([F:111])[C:108]([OH:110])=[O:109]>C(OCC)C>[F:106][C:107]([F:112])([F:111])[C:108]([O-:110])=[O:109].[C:80]([C@H:79]([CH2:87][OH:88])[NH:78][C:77](=[O:93])[C@H:9]([CH2:8][C:7]([OH:94])=[O:6])[NH:10][C:11](=[O:76])[CH2:12][NH:13][C:14](=[O:75])[C@H:15]([CH2:51][CH2:52][CH2:53][NH:54][C:55]([NH2:57])=[NH:56])[NH:16][C:17](=[O:50])[CH2:18][CH2:19][C:20](=[O:49])[O:21][CH2:22][O:23][C:24]1[CH:29]=[C:28]([N:30]2[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)[O+:27]=[C:26]2[C:36]([C:39]3[CH:48]=[CH:47][C:42]4[O:43][CH2:44][CH2:45][O:46][C:41]=4[CH:40]=3)=[CH:37][S:38][C:25]=12)([OH:86])=[O:81]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 178427509HCID 178427509, compound

Product 1

HCID 178512855HCID 178512855, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A vial was charged with a magnetic stirring bar, 7-((8S,14S,17S)-14-(2-tert-butoxy-2-oxoethyl)-17-(tert-butoxymethyl)-20,20-dimethyl-3,6,9,12,15,18-hexaoxo-8-(3-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)propyl)-2,19-dioxa-7,10,13,16-tetraazahenicosyloxy)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-morpholinothieno[3,2-b]pyran-4-ium chloride (83) (0.500 g, 0.364 mmol) and a solution of water (20 μL, 1.09 mmol) and triisopropyl silane (224 μL, 1.09 mmol) in trifluoroacetic acid (5.19 mL, 70 mmol). The reaction solution was magnetically stirred at room temperature. After 3 hours, the reaction solution was charged with ethyl ether (20 mL). The resulting precipitate was filtered, and purified by high-pressure liquid chromatography to give 7-((8S,14S,17S)-17-carboxy-14-(carboxymethyl)-8-(3-guanidinopropyl)-18-hydroxy-3,6,9,12,15-pentaoxo-2-oxa-7,10,13,16-tetraazaoctadecyloxy)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-morpholinothieno[3,2-b]pyran-4-ium trifluoroacetate (84) as a white solid.

Workup

  1. additionA vial was charged with a magnetic stirring bar
  2. filtrationThe resulting precipitate was filtered
  3. custompurified by high-pressure liquid chromatography

Sources & evidence

ORD record
ord-3e2763a19df44f608631c8a6e5d83f9d
Source dataset
uspto-grants-2013_10
Patent number
US08557807B2

Reaction notes

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