Sodium Thiosulfate → HCID 23648434, compound

HRID 1182317Notes

Reaction equation

HRID 1182317 reaction equation
[OH:1][C@@H:2]([C@@H:14]([NH:19][C:20](=[O:43])[O:21][C@H:22]([CH2:27][N:28]1[CH:32]=[C:31]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=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](CN1C=C(C2C=CC(C(F)(F)F)=CC=2)N=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:43])[O:21][C@H:22]([CH2:27][N:28]1[CH:32]=[C:31]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)[N:30]=[CH:29]1)[C:23]([CH3:25])([CH3:26])[CH3:24])[CH2:15][CH2:16][CH2:17][CH3:18])=[O:1])(=[O:6])=[O:7]

Participants

8

Reactant 5

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86596690HCID 86596690, compoundHCID 86596691HCID 86596691, compound

Product 1

HCID 23648434HCID 23648434, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.20 g (0.28 mmol) of (1S)-2,2-dimethyl-1-({4-[4-(trifluoromethyl)phenyl]-1H-imidazol-1-yl}methyl)propyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate and (1S)-2,2-dimethyl-1-({4-[4-(trifluoromethyl)phenyl]-1H-imidazol-1-yl}methyl)propyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate in 3 mL chloroform was added 0.15 g (0.35 mmol) Dess-Martin periodinane. The reaction mixture was stirred at room temperature for 1.5 h, then diluted with ethyl acetate and a saturated aqueous sodium thiosulfate solution. The layers were mixed vigorously, and then 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 83.2 mg (48%) of (1S)-2,2-dimethyl-1-({4-[4-(trifluoromethyl)phenyl]-1H-imidazol-1-yl}methyl)propyl (1S)-1-{[(2-pyridinylsulfonyl)amino]acetyl}pentylcarbamate. ES-LCMS m/z 624 (M+H) retention time=3.51 min. HRMS C29H36F3N5O5S m/z 624.2468 (M+H)Cal; 624.2463 (M+H)Obs.

Workup

  1. additionThe layers were mixed vigorously
  2. customThe layers were separated
  3. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with a methanol

Sources & evidence

ORD record
ord-63b0acf84f0f497fa10dffbde7faabce
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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