HCID 178501367, compound → HCID 178501493, compound

HRID 1177811Notes

Reaction equation

HRID 1177811 reaction equation
[CH3:1][O:2][C:3]([C@H:5]([NH:17]C(=O)OCC1C=CC=CC=1)[CH2:6][C:7]1[CH:15]=[C:14]([CH3:16])[C:10]2[NH:11][N:12]=[N:13][C:9]=2[CH:8]=1)=[O:4]>C(O)=O.CO>[NH2:17][C@H:5]([CH2:6][C:7]1[CH:15]=[C:14]([CH3:16])[C:10]2[NH:11][N:12]=[N:13][C:9]=2[CH:8]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

4

Reactant 1

HCID 178501367HCID 178501367, compound

Product 1

HCID 178501493HCID 178501493, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

Benzyl(R)-1-(methoxycarbonyl)-2-(7-methyl-1H-benzo[d][1,2,3]triazol-5-yl)ethylcarbamate (146 mg, 0.40 mmol) was dissolved in 12 mL of a solution of 4.4% formic acid in methanol. The reaction flask containing this solution was equipped with a magnetic stirbar and then flushed with nitrogen over several minutes. To the solution was added palladium on carbon (10%, 200 mg) and the reaction was stirred for 16 h at room temperature under nitrogen atmosphere. The reaction mixture was filtered through a pad of Celite® washing the pad several times with methanol. The filtrate was evaporated to give the title compound (quantitative yield). 1H-NMR (CDCl3, 300 MHz) δ 8.40 (bs, 1H), 7.55 (s, 1H), 7.14 (s, 1H), 4.29-4.24 (m, 1H), 3.78 (s, 3H), 3.39-3.19 (m, 2H), 2.69 (s, 3H). LC/MS: tR=1.18 min, 235 (MH)+.

Workup

  1. additionThe reaction flask containing this solution
  2. customwas equipped with a magnetic stirbar
  3. customflushed with nitrogen over several minutes
  4. additionTo the solution was added palladium on carbon (10%, 200 mg)
  5. filtrationThe reaction mixture was filtered through a pad of Celite®
  6. washwashing the pad several times with methanol
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-c27ecce9fa034aed9dee35ff2ed9cc6e
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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