Methyl 3-mercaptopropionate → HCID 67780360, compound

HRID 2400197Notes

Reaction equation

HRID 2400197 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]([C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=3)=[CH:19][CH:18]=2)[S:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S[CH2:41]CC(OC)=O>C(Cl)Cl.[Zn+2].[I-].[I-]>[CH3:41][O:15][C:14](=[O:16])[CH2:13][CH2:12][S:11][CH:10]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34](=[O:39])[C:35]([F:36])([F:37])[F:38])=[CH:30][CH:29]=2)=[CH:19][CH:18]=1)[CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 18050Methyl 3-mercaptopropionateHCID 19382503HCID 19382503, compound

Product 1

HCID 67780360HCID 67780360, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of the product of Step 4 (270 mg) and methyl 3-mercaptopropionate (250 mL) in 20 mL of CH2Cl2 was added ZnI2 (700 mg) at 0° C. The mixture was stirred for 20 min. at r.t. and then quenched with 20 mL of 25% NH4OAc, extracted with 100 mL of 2:1 Hexane/EtOAc. The organic extract was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography eluted with 5:1 Hexane/EtOAc to give 320 mg of the title compound.

Workup

  1. customquenched with 20 mL of 25% NH4OAc
  2. extractionextracted with 100 mL of 2:1 Hexane/EtOAc
  3. extractionThe organic extract
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluted with 5:1 Hexane/EtOAc

Sources & evidence

ORD record
ord-d57832a240ae4ddd99487804804bd8f0
Source dataset
uspto-grants-1995_09
Patent number
US05453443

Reaction notes

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