Triacetoxyperiodinane → HCID 89544846, compound

HRID 2283403Notes

Reaction equation

HRID 2283403 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C@H:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:31][CH3:32])=[C:26]([F:41])[C:25]=1[CH:42]([OH:51])[C:43]1[CH:44]=[N:45][C:46]([S:49][CH3:50])=[N:47][CH:48]=1>C(Cl)Cl>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C@H:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:31][CH3:32])=[C:26]([F:41])[C:25]=1[C:42]([C:43]1[CH:44]=[N:45][C:46]([S:49][CH3:50])=[N:47][CH:48]=1)=[O:51]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 89544283HCID 89544283, compound

Product 1

HCID 89544846HCID 89544846, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Step 2 Dess-Martin periodinane (243 mg, 0.572 mmol) was dissolved in dry CH2Cl2 (1 mL) and then added dropwise to a solution of tert-butyl N-[(1R)-1-(4-chloro-2-fluoro-3-{hydroxy[2-(methylsulfanyl)pyrimidin-5-yl]methyl}phenyl)propyl]carbamate (194 mg, 0.439 mmol) in dry CH2Cl2 (1 mL) and the solution was stirred at rt for 8 h. After this time the reaction mixture was diluted with CH2Cl2 (10 mL) and washed with saturated NaHCO3 (10 mL). The aqueous phase was extracted with CH2Cl2 (3×10 mL) and the combined organic extracts were washed with saturated Na2SO3 (10 mL) and brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo to give crude material (˜200 mg). Purified by silica column (25M on Biotage SP4) eluting 20-40% EtOAc in petroleum ether over 15 column volumes to give tert-butyl N-[(1R)-1-(4-chloro-2-fluoro-3-{[2-(methylsulfanyl)pyrimidin-5-yl]carbonyl}phenyl)propyl]-carbamate (100 mg, 0.23 mmol, 0.52%). m/z: 439.

Workup

  1. washwashed with saturated NaHCO3 (10 mL)
  2. extractionThe aqueous phase was extracted with CH2Cl2 (3×10 mL)
  3. washthe combined organic extracts were washed with saturated Na2SO3 (10 mL) and brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give crude material (˜200 mg)
  8. customPurified by silica column (25M on Biotage SP4)
  9. washeluting 20-40% EtOAc in petroleum ether over 15 column volumes

Sources & evidence

ORD record
ord-3c5c1f3e47b34495a1b2d53114a83dff
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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