HCID 67296679, compound → HCID 67313472, compound

HRID 1189963Notes

Reaction equation

HRID 1189963 reaction equation
[CH2:1]([CH:4]([CH2:25][CH2:26][CH3:27])[C:5]([NH:7][C:8]1[CH:9]=[C:10](/[CH:14]=[CH:15]/[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=[CH:12][CH:13]=1)=[O:6])[CH2:2][CH3:3]>C(O)C>[CH2:25]([CH:4]([CH2:1][CH2:2][CH3:3])[C:5]([NH:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=[CH:12][CH:13]=1)=[O:6])[CH2:26][CH3:27]

Participants

3

Reactant 1

HCID 67296679HCID 67296679, compound

Product 1

HCID 67313472HCID 67313472, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (E)-tert-butyl 3-(3-(2-propylpentanamido)phenyl)allylcarbamate (0.5 g, 1.32 mmol) in ethanol was degassed by bubbling argon for 2 min. Pd/C (10% wt, 0.5 g) was added and the reaction mixture atmosphere was changed to hydrogen by alternating between vacuum and hydrogen 2×. The reaction mixture was stirred under a H2-filled balloon for 16 h then filtered through Celite and the filtrate was concentrated under reduced pressure. Purification by column chromatography (100-200 mesh silica, 10% to 15% EtOAc in hexane) gave compound tert-butyl 3-(3-(2-propylpentanamido)phenyl)propylcarbamate as a thick yellow oil. Yield (0.5 g, 99%); 1H NMR (400 MHz, CDCl3) δ 7.45 (s, 1H), 7.31 (d, J=7.6 Hz, 1H), 7.22 (t, J=8.0 Hz, 1H), 7.08 (bs, 1H), 6.93 (d, J=7.6 Hz, 1H), 4.60 (bs, 1H), 3.15-3.14 (m, 2H), 2.62 (t, J=7.2 Hz, 2H), 2.49-2.16 (m, 1H), 1.82-1.72 (m, 2H), 1.72-1.66 (m, 2H), 1.37 (s, 9H), 1.36-1.22 (m, 6H), 0.92 (t, J=7.2 Hz, 6H).

Workup

  1. customby bubbling argon for 2 min
  2. additionPd/C (10% wt, 0.5 g) was added
  3. additionfilled balloon for 16 h
  4. filtrationthen filtered through Celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customPurification by column chromatography (100-200 mesh silica, 10% to 15% EtOAc in hexane)

Sources & evidence

ORD record
ord-8208140cf8bb486bb6a51e2651a8eb2d
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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