Sodium Thiosulfate → HCID 23648438, compound

HRID 1182313Notes

Reaction equation

HRID 1182313 reaction equation
[OH:1][C@@H:2]([C@@H:14]([NH:19][C:20](=[O:39])[O:21][C@H:22]([CH2:27][N:28]1[C:32]2[CH:33]=[C:34]([Cl:38])[C:35]([Cl:37])=[CH:36][C:31]=2[N:30]=[CH:29]1)[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:7])=[O:6].O[C@H]([C@@H](NC(=O)O[C@H](CN1C2C=C(Cl)C(Cl)=CC=2N=C1)C(C)(C)C)CCCC)CNS(C1C=CC=CN=1)(=O)=O.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[S:5]([NH:4][CH2:3][C:2]([C@@H:14]([NH:19][C:20](=[O:39])[O:21][C@H:22]([CH2:27][N:28]1[C:32]2[CH:33]=[C:34]([Cl:38])[C:35]([Cl:37])=[CH:36][C:31]=2[N:30]=[CH:29]1)[C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:15][CH2:16][CH2:17][CH3:18])=[O:1])(=[O:7])=[O:6]

Participants

8

Reactant 5

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 58981738HCID 58981738, compoundHCID 58981745HCID 58981745, compound

Product 1

HCID 23648438HCID 23648438, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 50.5 mg (0.084 mmol) of (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate & (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate in 2.2 mL of chloroform was added 44.6 mg (0.105 mmol) of Dess-Martin periodinane. The mixture was stirred at room temperature for 1.25 h, and then diluted with ethyl acetate. A saturated aqueous sodium thiosulfate solution was added, and the two layers were mixed vigorously before a saturated aqueous solution of sodium bicarbonate was added. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography eluting with a hexane:acetone solution (1:1) to yield 19 mg (38%) of (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S)-1-{[(2-pyridinylsulfonyl)amino]acetyl}pentylcarbamate. ES-LCMS m/z 598 (M+H)+ retention time=4.00 min. HRMS C26H33Cl2NS5O5S m/z 598.1658 (M+H)Cal; 598.1674 (M+H)Obs.

Workup

  1. additionwas added
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with a hexane

Sources & evidence

ORD record
ord-438f648f08e74356b9e05fbe3564b4f6
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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