Sodium Thiosulfate → HCID 89813056, compound

HRID 1481041Notes

Reaction equation

HRID 1481041 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:20])=[C:5]([C:21]([NH:23][CH2:24][CH2:25][C@H:26]([OH:31])[C:27]([O:29][CH3:30])=[O:28])=[O:22])[N:4]=1)#[N:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:11]=2)[C:6]([OH:20])=[C:5]([C:21]([NH:23][CH2:24][CH2:25][C:26](=[O:31])[C:27]([O:29][CH3:30])=[O:28])=[O:22])[N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 131736614HCID 131736614, compound

Product 1

HCID 89813056HCID 89813056, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-Methyl 4-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)-2-hydroxybutanoate (54 mg, 0.13 mmol) in anhydrous CH2Cl2 (5 mL) was added Dess-Martin periodinane (65 mg, 0.15 mmol). After stirring for 1 hour at room temperature, 2% Na2S2O3 (6 mL) was added and the resulting mixture was stirred at room temperature for 30 minutes. The layers were separated and the organic layer was washed with H2O, dried over MgSO4, concentrated, and purified by flash chromatography (0-20% EtOAc/CH2Cl2) to give the title compound in 34 mg. MS: (−) m/z 418.24 (M−1).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. customThe layers were separated
  3. washthe organic layer was washed with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography (0-20% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-b6a76fd422514550a26eb457e43ff7b3
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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