Hydrochloric Acid → HCID 68491094, compound

HRID 1822467Notes

Reaction equation

HRID 1822467 reaction equation
C([O:3][C:4]([C@@:6]1([NH:11][C:12](=[O:48])[C@@H:13]2[CH2:17][C@@H:16]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=4)[N:22]=[C:21]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:20]=3)[CH2:15][N:14]2[C:37]([NH:39][NH:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:38])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])C.[Li+].[OH-].Cl>C1COCC1.CO>[CH2:41]([NH:40][NH:39][C:37]([N:14]1[CH2:15][C@H:16]([O:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=3)[N:22]=[C:21]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:20]=2)[CH2:17][C@H:13]1[C:12]([NH:11][C@:6]1([C:4]([OH:5])=[O:3])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:48])=[O:38])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69030343HCID 69030343, compound

Product 1

HCID 68491094HCID 68491094, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution compound 106 (0.0101 mmol) in THF-MeOH 2:3 (3 ml) was added 1M LiOH 10 equiv. The solution was kept at 50° C. for 18 hrs. After cooling to RT the sample was neutralized with HCl and concentrated to dryness. The crude material was dissolved in DCM (2 ml) and a solution of TFA: TES 1:1 (1 ml) was added. The mixture was stirred for 3 hrs at RT and then concentrated to dryness. The crude material was dissolved in MeOH and purified by Prep LCMS which gave the title compound (0.6 mg). Purity by HPLC>95%. M+H+622.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe crude material was dissolved in DCM (2 ml)
  3. additiona solution of TFA: TES 1:1 (1 ml) was added
  4. concentrationconcentrated to dryness
  5. dissolutionThe crude material was dissolved in MeOH
  6. custompurified by Prep LCMS which

Sources & evidence

ORD record
ord-fe0700a80b5a4be59e235a233164b205
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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