Water → Methyl 4-(4-[[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)sulfanyl]methyl]-5-methyl-1,3-oxazol-2-yl)benzoate

HRID 931482

Reaktionsgleichung

Reaktionsgleichung von HRID 931482
CS(O[CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:8][CH2:7]1)(=O)=O.[CH3:20][C:21]1[O:25][C:24]([C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=2)=[N:23][C:22]=1[CH2:36][SH:37].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[C:15]([O:14][C:13]([NH:12][CH:9]1[CH2:8][CH2:7][CH:6]([S:37][CH2:36][C:22]2[N:23]=[C:24]([C:26]3[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=3)[O:25][C:21]=2[CH3:20])[CH2:11][CH2:10]1)=[O:19])([CH3:16])([CH3:17])[CH3:18]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 21882613trans-4-(Boc-amino)cyclohexyl methanesulfonateHCID 86709134Methyl 4-[5-methyl-4-(sulfanylmethyl)-1,3-oxazol-2-yl]benzoate

Produkt 1

HCID 68278174Methyl 4-(4-[[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)sulfanyl]methyl]-5-methyl-1,3-oxazol-2-yl)benzoateAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of tert-butyl N-[4-(methanesulfonyloxy)cyclohexyl]carbamate (2.24 g, 7.64 mmol, 1.00 equiv), methyl 4-[5-methyl-4-(sulfanylmethyl)-1,3-oxazol-2-yl]benzoate (3.0 g, 11.39 mmol, 1.20 equiv) and cesium carbonate (5.55 g, 16.98 mmol, 2.00 equiv) in N,N-dimethylformamide (30 mL) was stirred at 50° C. under nitrogen atmosphere for 3 h. Water (100 mL) was added to quench the reaction. The resulting solution was extracted with 3×80 mL of ethyl acetate. The combined organic layers was washed with 2×200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:15-2:1) to give 960 mg (27%) of methyl 4-(4-[[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)sulfanyl]methyl]-5-methyl-1,3-oxazol-2-yl)benzoate as a yellow solid. LC-MS: (ES, m/z): 461 [M+H]+, 405, 271, 230, 102.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionThe resulting solution was extracted with 3×80 mL of ethyl acetate
  4. washThe combined organic layers was washed with 2×200 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified on a silica gel column
  8. washeluted with ethyl acetate/petroleum ether (1:15-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-5fa763a6914b40b0a1db18179ad16f22
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296732B2

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