Sodium Thiosulfate → HCID 58981693, compound

HRID 1182319Notes

Reaction equation

HRID 1182319 reaction equation
[OH:1][C@H:2]([C@@H:14]([NH:19][C:20](=[O:40])[O:21][C@H:22]([CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]2[CH:39]=[CH:38][N:37]=[CH:36]2)=[CH:31][CH:30]=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](COC1C=CC(N2C=CN=C2)=CC=1)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:40])[O:21][C@H:22]([CH2:27][O:28][C:29]1[CH:30]=[CH:31][C:32]([N:35]2[CH:39]=[CH:38][N:37]=[CH:36]2)=[CH:33][CH:34]=1)[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:15][CH2:16][CH2:17][CH3:18])=[O:1])(=[O:6])=[O:7]

Participants

8

Reactant 5

HCID 24477Sodium ThiosulfateHCID 159087Triacetoxyperiodinane2×HCID 516892Sodium BicarbonateHCID 58981730HCID 58981730, compoundHCID 58981737HCID 58981737, compound

Product 1

HCID 58981693HCID 58981693, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 96.6 mg (0.17 mmol) of (1S)-1-{[4-(1H-imidazol-1-yl)phenoxy]methyl}-2,2-dimethylpropyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate & (1S)-1-{[4-(1H-imidazol-1-yl)phenoxy]methyl}-2,2-dimethylpropyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate in 1.7 mL of chloroform was added 85 mg (0.2 mmol) of Dess-Martin periodinane, and the mixture was stirred at room temperature for 1 h. A second portion of 15 mg (0.035 mmol) of Dess-Martin periodinane was added, and the reaction mixture was stirred for 0.5 h. It was then diluted with ethyl acetate and a saturated aqueous sodium thiosulfate solution. The layers were mixed vigorously, before a saturated aqueous sodium bicarbonate solution was added. The layers were separated, and the organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography eluting with a methanol:chloroform solution (1:9) to yield 21.6 mg (23%) of (1S)-1-{[4-(1H-imidazol-1-yl)phenoxy]methyl}-2,2-dimethylpropyl (1S)-1-{[(2-pyridinylsulfonyl)amino]acetyl}pentylcarbamate. ES-LCMS m/z 572 (M+H) retention time=2.83 min. HRMS C28H37N5O6S m/z 572.2543 (M+H)Cal; 572.2526 (M+H)Obs.

Workup

  1. stirringthe reaction mixture was stirred for 0.5 h
  2. additionwas added
  3. customThe layers were separated
  4. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a methanol

Sources & evidence

ORD record
ord-067ae65b11dc40788d52fe0c3a4ca94e
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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