HCID 11200815, compound → HCID 11198120, compound

HRID 2243835Notes

Reaction equation

HRID 2243835 reaction equation
[C:1]([N:6]1[C@@:10]2([CH2:14][CH2:13][N:12]([C@@H:15]([C:20]([O:22]CC3C=CC=CC=3)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[C:11]2=[O:30])[CH2:9][CH2:8][CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]>CO>[C:1]([N:6]1[C@@:10]2([CH2:14][CH2:13][N:12]([C@@H:15]([C:20]([OH:22])=[O:21])[CH2:16][CH:17]([CH3:18])[CH3:19])[C:11]2=[O:30])[CH2:9][CH2:8][CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 11200815HCID 11200815, compound

Product 1

HCID 11198120HCID 11198120, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A degassed solution of 13 (134 mg, 0.32 mmol) in methanol containing 10% Pd/C (27 mg) was hydrogenated under 16 psi for 24 h. The mixture was filtered through a pad of celite and the filtered solution was concentrated under reduced pressure to afford 16 (100 mg, 95%) as a colourless oil. M.p. 68-69° C. [α]20D −2° (c 1.1, MeOH). 1H-NMR [300 MHz, acetone-d6] δ 0.87-0.91 (2d, J=7, 6H), 1.09-1.12 (2d, 6H), 1.46 (m, 1H), 1.70 (m, 2H), 1.90-2.10 (m, 5H), 2.49 (m, 1H), 2.70 (m, 1H), 3.30 (m, 1H), 3.49 (dt, J1=8, J2=10, 1H), 3.61-3.75 (m, 2H), 4.71 (dd, J1=5, J2=11, 1H). 13C-NMR (75 MHz, CDCl3) δ 16.4, 16.6, 21.1, 23.0, 24.3, 25.0, 30.8, 32.6, 36.6, 36.9, 40.6, 48.0, 53.4, 67.5, 171.8, 174.2, 176.2. ESI-MS Calcd for C17H28N2O4: 324.20. Found: 323.3 (M−1)+.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtered solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-83dc96e751cd4d089a9d17fa9aee7b78
Source dataset
uspto-grants-2010_03
Patent number
US07678765B2

Reaction notes

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