Acetic Acid → HCID 68548528, compound

HRID 1158610Notes

Reaction equation

HRID 1158610 reaction equation
[CH3:1][O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:15](=[O:16])[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[C:25][CH2:26][NH:27]C(OCC4C=CC=CC=4)=O)[CH:19]=3)([CH3:17])[NH:13][C:12]2=[O:38])[CH:5]=1.C(O)(=O)C>CO.[Pd]>[CH3:1][O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:15](=[O:16])[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][CH2:26][NH2:27])[CH:19]=3)([CH3:17])[NH:13][C:12]2=[O:38])[CH:5]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59513421HCID 59513421, compound

Product 1

HCID 68548528HCID 68548528, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the Cbz-protected propargylamine 3 (580 mg, 1.1 mmol) and acetic acid (50 μL) in MeOH (10 mL) was stirred over 10% Pd/C (284 mg) under an atmosphere of hydrogen (50 psi) for 18 h. The suspension was passed through a PTFE-filter and the resulting filtrate concentrated under vacuum to give the desired material as a yellow solid (440 mg, 100%). 1H NMR (400 MHz, CDCl3) δ 8.32 (bs, 1H), 8.05 (bs, 2H), 7.83-7.88 (m, 2H), 7.34-7.41 (m, 3H), 7.27 (m, 1H), 7.14 (m, 1H), 6.95 (m, 1H), 4.57 (s, 2H), 3.79 (s, 3H), 3.39 (m, 2H), 2.86 (m, 2H), 2.60 (m, 2H), 2.00 (m, 2H), 1.65 (s, 3H). MS (ES+): 396 (M+H), 418 (M+Na).

Workup

  1. filtrationfilter
  2. concentrationthe resulting filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-dec1635801f1418493d9822df41ab1df
Source dataset
uspto-grants-2010_10
Patent number
US07812013B2

Reaction notes

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