HCID 131733446, compound → HCID 131733445, compound

HRID 2277068Notes

Reaction equation

HRID 2277068 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[O:12]=[S:13]1(=[O:41])[CH2:18][CH2:17][CH:16]([CH2:19][S:20]([C:23]2[CH:24]=[C:25]([CH:29]([OH:40])[CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH:26]=[CH:27][CH:28]=2)(=[O:22])=[O:21])[CH2:15][CH2:14]1>C(Cl)Cl>[O:41]=[S:13]1(=[O:12])[CH2:18][CH2:17][CH:16]([CH2:19][S:20]([C:23]2[CH:24]=[C:25]([C:29](=[O:40])[CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])[CH:26]=[CH:27][CH:28]=2)(=[O:21])=[O:22])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 131733446HCID 131733446, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 131733445HCID 131733445, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (218 mg, 1.01 mmol) and molecular sieves were added to a solution of tert-butyl (3-(3-(((1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methyl)sulfonyl)phenyl)-3-hydroxypropyl)carbamate (650 mg, 1.40 mmol) in CH2Cl2 (20 mL) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was filtered through a Celite, the filtrate was diluted with EtOAc, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (60% EtOAc-hexanes gradient) gave tert-butyl (3-(3-(((1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methyl)sulfonyl)phenyl)-3-oxopropyl)carbamate as a colorless liquid. Yield (0.438 g, 67%); 1H NMR (400 MHz, DMSO-d6): δ 8.36 (s, 1H), 8.28 (d, J=7.6 Hz, 1H), 8.16 (d, J=7.6 Hz, 1H), 7.83 (t, J=8.0 Hz, 1H), 6.87 (s, 1H), 3.51 (d, J=6.4 Hz, 2H), 3.32-3.28 (m, 4H), 3.28-3.23 (m, 2H), 3.20-3.13 (m, 1H), 3.04-3.01 (m, 1H), 2.32 (bs, 1H), 2.17-2.14 (m, 2H), 1.85-1.76 (m, 2H), 1.35 (s, 9H); MS: m/z 460.23 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through a Celite
  2. additionthe filtrate was diluted with EtOAc
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (60% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-c7d5700bd78a405a97cfef04a386a782
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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