HCID 68709991, compound → HCID 58864502, compound

HRID 1177684Notes

Reaction equation

HRID 1177684 reaction equation
[CH3:1][O:2][C:3](=[O:36])[CH:4]([NH:25]C(OCC1C=CC=CC=1)=O)[CH2:5][C:6]1[CH:14]=[C:13]([CH3:15])[C:12]2[C:8](=[CH:9][N:10]([S:16]([CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])(=[O:18])=[O:17])[N:11]=2)[CH:7]=1.[H][H]>[Pd].CO>[CH3:1][O:2][C:3](=[O:36])[C@H:4]([NH2:25])[CH2:5][C:6]1[CH:14]=[C:13]([CH3:15])[C:12]2[C:8](=[CH:9][N:10]([S:16]([CH2:19][CH2:20][Si:21]([CH3:22])([CH3:24])[CH3:23])(=[O:17])=[O:18])[N:11]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 68709991HCID 68709991, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58864502HCID 58864502, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Benzyloxycarbonylamino-3-[7-methyl-2-(2-trimethylsilanyl-ethanesulfonyl)-2H-indazol-5-yl]-propionic acid methyl ester, (1.35 g, 2.54 mmol) and 10% palladium on carbon (135 mg) in methanol (40 mL) were agitated for 3.0 h under 55 psi hydrogen using a Parr apparatus. 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 the title compound (1.01 g, quantitative yield) as a sticky gum. 1H-NMR (CDCl3, 300 MHz) δ 8.45 (s, 1H), 7.29 (s, 1H), 6.97 (s, 1H), 3.79-3.73 (m, 1H), 3.73 (s, 3H), 3.56-3.50 (m, 2H), 5.12 (dd, J=13.5, 5.12 Hz, 1H), 4.85 (dd, J=13.5, 8.1 Hz, 1H), 2.58 (s, 3H), 0.87-0.81 (m, 2H), 0.01 (s, 9H). 13C-NMR (CDCl3, 75 MHz) δ 175.5, 151.8, 133.7, 129.9, 129.4, 125.0, 121.3, 117.9, 55.5, 52.1, 51.1, 41.4, 17.1, 9.8, −2.1. Mass spec.: 398 (MH)+.

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-fe2d86219e274a108720fa39d177eada
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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