Ethyl 3-mercaptopropionate → HCID 66756713, compound

HRID 1642639Notes

Reaction equation

HRID 1642639 reaction equation
[H-].[Na+].C(OC(=O)CC[SH:9])C.[CH2:11]([O:18][C:19]1[CH:24]=[C:23](F)[CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.OC1C=CC=C(CC2C=CC(N3CC(=O)NS3(=O)=O)=C(O)C=2)C=1C#N>CN(C=O)C.CCOC(C)=O>[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([SH:9])[CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 21625Ethyl 3-mercaptopropionateHCID 24758Sodium hydrideHCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzeneHCID 17747051HCID 17747051, compound

Product 1

HCID 66756713HCID 66756713, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of NaH (60%, 1.21 g, 30.3 mmol) in dry DMF (20 mL) under N2 at 0° C. is added dropwise 3-mercaptopropionic acid ethyl ester (1.9 mL, 15.2 mmol) and 2-benzyloxy-4-fluoro-1-nitrobenzene (intermediate from Example 27) (2.5 g, 10.1 mmol) in dry DMF (10 mL). The reaction is allowed to warm to ambient temperature and stirred for 4 days. The mixture is then diluted with EtOAc (100 mL) and extracted with 1N HCl (50 mL). The organics are washed with brine and dried with Na2SO4. Evaporation yields a yellow oil which is purified by flash chromatography (30-50% EtOAc). The title compound is isolated as a yellow oil: MS (M−H)−=260.2.

Workup

  1. extractionextracted with 1N HCl (50 mL)
  2. washThe organics are washed with brine
  3. dry with materialdried with Na2SO4
  4. customEvaporation
  5. customyields a yellow oil which
  6. customis purified by flash chromatography (30-50% EtOAc)

Sources & evidence

ORD record
ord-119075406729428fb61cf4812089952a
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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