Hydrochloric Acid → HCID 86587454, compound

HRID 2084558Notes

Reaction equation

HRID 2084558 reaction equation
C([S:4][CH2:5][CH:6]([CH:40]1[C:48]2[C:43](=[CH:44][C:45]([Br:49])=[CH:46][CH:47]=2)[CH2:42][CH2:41]1)[C:7]([NH:9][CH:10]([CH2:15][C:16]1[N:17]=[CH:18][N:19]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=1)[C:11]([O:13]C)=[O:12])=[O:8])(=O)C.[OH-].[Na+].Cl>CO>[Br:49][C:45]1[CH:44]=[C:43]2[C:48](=[CH:47][CH:46]=1)[CH:40]([CH:6]([CH2:5][SH:4])[C:7]([NH:9][C@H:10]([C:11]([OH:13])=[O:12])[CH2:15][C:16]1[N:17]=[CH:18][N:19]([C:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:20]=1)=[O:8])[CH2:41][CH2:42]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22732587HCID 22732587, compound

Product 1

HCID 86587454HCID 86587454, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound obtained in Example 37 is dissolved in 5 ml of degassed methanol. After 10 minutes' stirring at room temperature, 4 eq. of a degassed 1M sodium hydroxide solution are, added to that solution. The resulting solution is stirred at room temperature under argon for 5 hours. The progress of the reaction is monitored by HPLC. When the reaction is complete, the solution is rendered acidic to pH=1 with 1N hydrochloric acid. The methanol is removed in vacuo, 10 ml of water are added to the residue and extraction is carried out with 10 ml of chloroform. The organic phase is separated off, dried over Na2SO4, concentrated in vacuo and purified by HPLC chromatography.

Workup

  1. additionadded to that solution
  2. stirringThe resulting solution is stirred at room temperature under argon for 5 hours
  3. customThe methanol is removed in vacuo, 10 ml of water
  4. additionare added to the residue and extraction
  5. customThe organic phase is separated off
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by HPLC chromatography

Sources & evidence

ORD record
ord-761dacd37a9f4c628083af46053d7c97
Source dataset
uspto-grants-2004_04
Patent number
US06716852B2

Reaction notes

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