3-Sulfanyloxolan-2-one → HCID 58392663, compound

HRID 446852Notes

Reaction equation

HRID 446852 reaction equation
[CH2:1]([N:8]1[CH2:32][C@:31]2([C:33](O)=[O:34])[C@@H:10]([CH2:11][C@H:12]3[CH:25]4[C@@:16]([F:29])([C@:17]5([CH3:28])[C:22]([C@@H:23]([F:26])[CH2:24]4)=[CH:21][C:20](=[O:27])[CH:19]=[CH:18]5)[C@@H:15]([OH:30])[CH2:14][C@@:13]32[CH3:36])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:37][CH:38]1[CH2:42][CH2:41][O:40][C:39]1=[O:43]>CN(C=O)C.CN(C)C1C=CN=CC=1.CCOC(C)=O>[O:43]=[C:39]1[CH:38]([S:37][C:33]([C@:31]23[C@@:13]4([CH3:36])[CH2:14][C@H:15]([OH:30])[C@@:16]5([F:29])[C@H:25]([C@@H:12]4[CH2:11][C@H:10]2[CH2:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:32]3)[CH2:24][C@H:23]([F:26])[C:22]2[C@:17]5([CH3:28])[CH:18]=[CH:19][C:20](=[O:27])[CH:21]=2)=[O:34])[CH2:42][CH2:41][O:40]1

Participants

6

Reactant 2

HCID 1396663-Sulfanyloxolan-2-oneHCID 67352569HCID 67352569, compound

Product 1

HCID 58392663HCID 58392663, compoundYield 13.14%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound 93 and 1,1-carbonyldiimidazole (74.3 mg, 0.458 mmol) in dry DMF (3 ml) is stirred under nitrogen at RT for 1 hour and at 65° C. for 1 hour 30 minutes. The mixture is cooled to RT and 4-dimethylaminopyridine (46.7 mg, 0.382 mmol) and a solution of 3-mercaptodihydrofuran-2(3H)-one (54.1 mg, 0.458 mmol) in dry DMF (1.2 ml) are added. The mixture is stirred at RT for 1 hour then at 70° C. for 48 hours. The mixture is diluted with AcOEt and washed with brine. The organic phase is dried over Na2SO4 and filtered. The solvent is evaporated to give a brown oil which is purified by silica gel chromatography (AcOEt/petroleum ether 45/55) to afford the title compound (30 mg, 0.050 mmol, 13.14% yield).

Workup

  1. waitat 70° C. for 48 hours
  2. washwashed with brine
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent is evaporated
  6. customto give a brown oil which
  7. customis purified by silica gel chromatography (AcOEt/petroleum ether 45/55)

Sources & evidence

ORD record
ord-1890b570f9d541c1ba5ac9dd81d1e1d0
Source dataset
uspto-grants-2013_07
Patent number
US08481517B2

Reaction notes

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