2-Furanmethanethiol → (S)-3-tert-butoxycarbonylamino-1-furfurylthio-2-heptanone

HRID 1683956Notes

Reaction equation

HRID 1683956 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][CH2:16][CH3:17])[C:10](=[O:13])[CH2:11]Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([SH:24])[C:19]1[O:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][CH2:16][CH3:17])[C:10](=[O:13])[CH2:11][S:24][CH2:18][C:19]1[O:23][CH:22]=[CH:21][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 73632-FuranmethanethiolHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 15287852(s)-3-Tert-butoxycarbonylamino-1-chloro-2-heptanone

Product 1

HCID 15287853(S)-3-tert-butoxycarbonylamino-1-furfurylthio-2-heptanoneYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (s)-3-tert-butoxycarbonylamino-1-chloro-2-heptanone (6.54 g) and furfurylmercaptan (3.11 g) in tetrahydrofuran (200 ml) was added 2N sodium hydroxide (13 ml), and the mixture was stirred at room temperature for 17 hours. Then, aqueous sodium hydrogencarbonate was added to the mixture, which was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and chromatographed on a silica gel column, eluting with hexane containing 10% ethyl acetate to give the titled product (7.82 g).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customchromatographed on a silica gel column
  7. washeluting with hexane containing 10% ethyl acetate

Sources & evidence

ORD record
ord-e3e0b53833404d4785b9117e356f3f7f
Source dataset
uspto-grants-1997_06
Patent number
US05639783

Reaction notes

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