Hydrochloric Acid → HCID 68638958, compound

HRID 1354984Notes

Reaction equation

HRID 1354984 reaction equation
C(S[C:9](=[O:46])[CH:10]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH:11]([OH:38])[CH:12]=[CH:13][CH:14]([OH:37])[CH2:15][CH:16]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:20][CH:19]=1)C1C=CC=CC=1.[Li+].[OH-:48].OO.Cl>C1COCC1>[CH2:39]([CH:10]([CH:11]([OH:38])[CH:12]=[CH:13][CH:14]([OH:37])[CH2:15][CH:16]([NH:29][C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[CH:20][CH:19]=1)[C:9]([OH:46])=[O:48])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 72447983HCID 72447983, compound

Product 1

HCID 68638958HCID 68638958, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

16 stereoisomers of 50 were synthesized by the following procedure: To a solution of 49 (1.0 equiv) in THF (60 mL/mmol) was added 0.2 N LiOH (aq) (2.0 equiv) and 30% H2O2 (aq) (equal volume to LiOH (aq)). The solution was stirred for 3 h at room temperature, then acidified with 1 N HCl (aq) to pH=1 and extracted with CH2Cl2. The organic solution was dried over Na2SO4, concentrated under reduced pressure, and purified by flash chromatography to afford 50 in 64–84% yield on 0.020 to 0.030 mmol scale.

Workup

  1. custom16 stereoisomers of 50 were synthesized by the following procedure
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic solution was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c0cb02bc495b4037af57857a5db373b1
Source dataset
uspto-grants-2007_05
Patent number
US07223888B2

Reaction notes

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