HCID 57999634, compound → HCID 42641554, compound

HRID 600315Notes

Reaction equation

HRID 600315 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:11][C:12]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2C(OC(C)(C)C)=O)=[O:13])[C:9]#[N:10])=[CH:3][CH:2]=1>C(O)=O>[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@H:8]([NH:11][C:12]([C@@H:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)=[O:13])[C:9]#[N:10])=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 57999634HCID 57999634, compound

Product 1

HCID 42641554HCID 42641554, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (S)-tert-butyl 2-((S)-2-(biphenyl-4-yl)-1-cyanoethylcarbamoyl)pyrrolidine-1-carboxylate (178 mg) in formic acid (5 mL) was stirred and heated at 50° C. for 10 min. The solvent was evaporated. The crude material was dissolved in methanol (2 mL) and loaded on to a 10 g SCX cartridge. The impurities were washed through with methanol (20 mL) and discarded. The product was eluted with 0.7 N methanolic ammonia (15 mL) and evaporated in vacuo. The residue was triturated with ethyl acetate (3 mL) and the solid collected, washed with a little ethyl acetate and dried to afford the title compound (92 mg).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe crude material was dissolved in methanol (2 mL)
  3. washThe impurities were washed through with methanol (20 mL)
  4. washThe product was eluted with 0.7 N methanolic ammonia (15 mL)
  5. customevaporated in vacuo
  6. customThe residue was triturated with ethyl acetate (3 mL)
  7. customthe solid collected
  8. washwashed with a little ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-226ec2fcb5614b959cc373a0e9414b73
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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