2-benzyloxycarbonylamino-3-(7-methyl-1H-indazol-5-yl)-acrylic acid methyl ester → methyl 2-amino-3-(7-methyl-1H-indazol-5-yl)propanoate

HRID 1353520Notes

Reaction equation

HRID 1353520 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]([NH:16]C(OCC1C=CC=CC=1)=O)=[CH:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[NH:11][N:10]=[CH:9]2>CO>[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH2:16])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[NH:11][N:10]=[CH:9]2

Participants

3

Reactant 1

HCID 684655482-benzyloxycarbonylamino-3-(7-methyl-1H-indazol-5-yl)-acrylic acid methyl ester

Product 1

HCID 58864334methyl 2-amino-3-(7-methyl-1H-indazol-5-yl)propanoateYield 115%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-benzyloxycarbonylamino-3-(7-methyl-1H-indazol-5-yl)-acrylic acid methyl ester (4.93 g, 13.49 mmol) in methanol (125 mL) was degassed by bubbling nitrogen through it for 30 min and then 10% palladium on charcoal (0.6 g) was carefully added. The mixture was hydrogenated at 40 psi in a Parr shaker apparatus overnight. The catalyst was removed by filtration through a pad of celite and the filtrate was concentrated in vacuo to give the product as a colorless foam (3.62 g, quant.). 1H-NMR (CD3OD, 500 MHz) δ 2.45 (3H, s), 2.99 (1H, Abq), 3.22 (1H, Abq), 3.74 (3H, s), 3.89 (1H, m), 6.91 (1H, s), 7.31 (1H, s), 7.73 (1H, s). Mass spec.: 234.11 (MH)+.

Workup

  1. customby bubbling nitrogen through it for 30 min
  2. addition10% palladium on charcoal (0.6 g) was carefully added
  3. customwas hydrogenated at 40 psi in a Parr shaker apparatus overnight
  4. customThe catalyst was removed by filtration through a pad of celite
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9b784f2951c84db09d1c5f8265f68946
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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