HCID 86666037, compound → HCID 67953269, compound

HRID 469742Notes

Reaction equation

HRID 469742 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][C@@H:16]([OH:18])[CH2:15][N:14]2[C:19]2[CH:24]=[CH:23][N:22]=[C:21](Cl)[N:20]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][C@@H:16]([OH:18])[CH2:15][N:14]2[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][N:20]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86666037HCID 86666037, compound

Product 1

HCID 67953269HCID 67953269, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (40 mg) is added to a solution of (2S,4R)-1-(2-chloro-pyrimidin-4-yl)-4-hydroxy-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide (100 mg, 0.273 mmol) in ethanol (2 mL). The reaction is stirred under hydrogen atmosphere overnight at room temperature. The reaction is filtered through Celite® and the filtrate is concentrated. Purification by pre-HPLC eluting with 4-45% acetonitrile/water provides the title compound. ESI m/z 332 [M+H+].

Workup

  1. filtrationThe reaction is filtered through Celite®
  2. concentrationthe filtrate is concentrated
  3. customPurification
  4. washby pre-HPLC eluting with 4-45% acetonitrile/water

Sources & evidence

ORD record
ord-cb44b50a9a1a4cc9a557f243b683f0fe
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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