HCID 25136279, compound → HCID 58864443, compound

HRID 1353510Notes

Reaction equation

HRID 1353510 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C@H:4]([NH:24]C(OCC1C=CC=CC=1)=O)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([S:15]([CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])(=[O:17])=[O:16])[N:10]=[CH:9]2.[H][H]>[Pd].CO>[CH3:1][O:2][C:3](=[O:35])[C@H:4]([NH2:24])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([S:15]([CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])(=[O:16])=[O:17])[N:10]=[CH:9]2

Participants

5

Reactant 2

HCID 25136279HCID 25136279, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58864443HCID 58864443, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-2-Benzyloxycarbonylamino-3-[1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazol-5-yl]-propionic acid methyl ester (1.24 g, 2.40 mmol) and 10% palladium on carbon (124 mg) in methanol (50 mL) was agitated for 2 h under 50 psi hydrogen using a Parr hydrogenator. The reaction mixture was purged with 3 vacuum/nitrogen purge cycles. The reaction mixture was then filtered through a pad of celite and the pad was rinsed with several portions of methanol. The methanol filtrate was evaporated to give 879 mg (96%) of the title compound as a sticky gum. 1H-NMR (CDCl3, 300 MHz) δ 8.21 (s, 1H), 8.02 (d, J=8.8 Hz, 1H), 7.59 (s, 1H), 7.38 (d, J=8.8 Hz, 1H), 3.72 (s, 3H), 3.38–3.32 (m, 2H), 3.21 (dd, J=13.9, 5.1 Hz, 1H), 2.98 (dd, J=13.9, 7.9 Hz, 1H), 0.91–0.85 (m, 2H), −0.02 (s, 9H).

Workup

  1. customThe reaction mixture was purged with 3 vacuum/nitrogen
  2. custompurge cycles
  3. filtrationThe reaction mixture was then filtered through a pad of celite
  4. washthe pad was rinsed with several portions of methanol
  5. customThe methanol filtrate was evaporated

Sources & evidence

ORD record
ord-ecff66d9583f4f738f5a7192cd8ddccf
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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