Methanol → HCID 57998022, compound

HRID 2425789Notes

Reaction equation

HRID 2425789 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)([S:16][CH3:17])[CH2:13][C@H:12]1[C:30]([OH:32])=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33]O>>[C:21]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:19][C:18]([C@@:14]2([S:16][CH3:17])[CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[C@H:12]([C:30]([O:32][CH3:33])=[O:31])[CH2:13]2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 57998006HCID 57998006, compound

Product 1

HCID 57998022HCID 57998022, compoundYield 90%

Procedure

To an iced colorless solution of (2S,4R)-1-(benzyloxycarbonyl)-4-(biphenyl-4-yl)-4-(methylthio)pyrrolidine-2-carboxylic acid (288 mg, 0.644 mmol) in MeOH (5 mL) was added (trimethylslyl)diazomethane (3.54 mL, 7.08 mmol) dropwise until it turned into light yellow (bubble was generated). The formed light yellow solution was stirred at room temperature overnight. Diluted with EtOAc, washed with 5% citric acid, and brine, dried over MgSO4, filtered, evaporated, to afford the desired product (2S,4R)-1-benzyl 2-methyl 4-(biphenyl-4-yl)-4-(methylthio)pyrrolidine-1,2-dicarboxylate (267 mg, 0.578 mmol, 90% yield) as a white wax. LC-MS (retention time: 3.25 min, method B), MS m/z 462 (M+H), 414 (M-MeSH).

Workup

  1. customturned into light yellow (bubble was generated)
  2. additionDiluted with EtOAc
  3. washwashed with 5% citric acid, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6488174007764761be85bff8f5bf49a7
Source dataset
uspto-grants-2011_06
Patent number
US07964560B2

Reaction notes

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