Phosphoric Acid → HCID 68494543, compound

HRID 1966505Notes

Reaction equation

HRID 1966505 reaction equation
Cl.C([O:4][C:5]([C@@:7]12[CH2:22][C@H:21]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]([NH:23][C:24]([C:26]1[CH:31]=[N:30][C:29]([CH3:32])=[CH:28][N:27]=1)=[O:25])[C:12](=[O:33])[N:11]1[CH2:34][C@H:35]([O:37][C:38]3[N:39]=[C:40]4[C:45](=[C:46]5[C:51]=3[CH:50]=[CH:49][CH:48]=[CH:47]5)[CH:44]=[CH:43][CH:42]=[CH:41]4)[CH2:36][C@H:10]1[C:9](=[O:52])[NH:8]2)=[O:6])C.O[Li].O.OP(O)(O)=O.[Na+].[Cl-].CC1CCCO1>O.O1CCCC1>[CH2:7]([NH:8][CH2:9][CH3:10])[CH3:5].[CH3:32][C:29]1[N:30]=[CH:31][C:26]([C:24]([NH:23][C@@H:13]2[C:12](=[O:33])[N:11]3[CH2:34][C@H:35]([O:37][C:38]4[N:39]=[C:40]5[C:45](=[C:46]6[C:51]=4[CH:50]=[CH:49][CH:48]=[CH:47]6)[CH:44]=[CH:43][CH:42]=[CH:41]5)[CH2:36][C@H:10]3[C:9](=[O:52])[NH:8][C@:7]3([C:5]([OH:6])=[O:4])[CH2:22][C@H:21]3[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:25])=[N:27][CH:28]=1

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 5234Sodium ChlorideHCID 73012-MethyltetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68496037HCID 68496037, compound

Product 1

HCID 68494543HCID 68494543, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The isolated product of Example 49c can be mixed with tetrahydrofuran, water and LiOH.H2O, and then heated and stirred. The reaction mixture can be later cooled, added with aqueous H3PO4, aqueous NaCl and 2-methyl tetrahydrofuran, and the organic layer is separated, washed and filtered. MeCN is added to the concentrated organic layer, heated and cooled, and then diethylamine is added. The slurry is heated and cooled to form (2R,6S,13aS,14aR,16aS,Z)-6-(5-Methylpyrazine-2-carboxamido)-5,16-dioxo-2-(phenanthridin-6-yloxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate diethylamine salt, which can be further washed and dried.

Workup

  1. temperatureheated
  2. temperatureThe reaction mixture can be later cooled
  3. customthe organic layer is separated
  4. washwashed
  5. filtrationfiltered
  6. additionMeCN is added to the concentrated organic layer
  7. temperatureheated
  8. temperaturecooled
  9. additiondiethylamine is added
  10. temperatureThe slurry is heated
  11. temperaturecooled

Sources & evidence

ORD record
ord-07b19764537144b886a78e7d6180033d
Source dataset
uspto-grants-2013_04
Patent number
US08420596B2

Reaction notes

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