Sodium Thiosulfate → HCID 59570844, compound

HRID 2071175Notes

Reaction equation

HRID 2071175 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]([N:15]2[CH2:19][CH2:18][CH2:17][C@@H:16]2[C:20]2[S:21][CH:22]=[C:23]([CH3:25])[N:24]=2)=[O:14])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:2]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]([N:15]2[CH2:19][CH2:18][CH2:17][C@@H:16]2[C:20]2[S:21][CH:22]=[C:23]([CH3:25])[N:24]=2)=[O:14])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:1]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 59570826HCID 59570826, compound

Product 1

HCID 59570844HCID 59570844, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-methyl 3-(hydroxymethyl)-5-(2-(4-methylthiazol-2-yl)pyrrolidine-1-carbonyl)benzoate (560 mg, 1.554 mmol) in DCM (60 mL), Dess-Martin periodinane (790.8 mg, 1.864 mmol) was added at rt. After stirring for 2 hrs, the mixture was poured into a mixture of aqueous 1 M Na2S2O3 (30 mL) and aqueous saturated NaHCO3 (30 mL), and it was extracted with DCM three times. The combined organic layers were concentrated in vacuum and the residue was purified by flash silica chromatography to give the product (530 mg). 1H NMR (CDCl3): d: 10.094, 9.933 (s, s, 1H), 8.592-7.908 (m, 3H), 6.796 (s, 1H), 5.661 (m, 0.65H), 5.083 (m, 0.35H), 3.969-3.743 (m, 4H), 3.515 (m, 1H), 2.429-2.308 (m, 5H), 2.145-1.939 (m, 2H).

Workup

  1. extractionwas extracted with DCM three times
  2. concentrationThe combined organic layers were concentrated in vacuum
  3. customthe residue was purified by flash silica chromatography

Sources & evidence

ORD record
ord-948c961c0e0e4d4b8230a1ee0c426e2f
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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