HCID 67408937, compound → HCID 67407233, compound

HRID 1949659Notes

Reaction equation

HRID 1949659 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH:13]2[N:16]([C:19](=[O:34])[CH:20]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[NH:21][C:22](=[O:27])[CH:23]([NH:25][CH3:26])[CH3:24])[CH2:17][CH2:18][CH:12]12)=O)C1C=CC=CC=1>CO>[CH:28]1([CH:20]([NH:21][C:22](=[O:27])[CH:23]([NH:25][CH3:26])[CH3:24])[C:19]([N:16]2[CH2:17][CH2:18][CH:12]3[NH:11][CH2:15][CH2:14][CH:13]23)=[O:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

3

Reactant 1

HCID 67408937HCID 67408937, compound

Product 1

HCID 67407233HCID 67407233, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 mL Parr bottle was charged with 117 (190 mg, 0.40 mmol) and 10% Pd-on-carbon (˜0.5 g) in MeOH (20 mL). The bottle was pressurized to 55 PSI H2 (379.2 KPa) and shaken for 3 h. The catalyst was removed by filtration through diatomaceous earth (Celite®) and washed with EtOAc and MeOH. The filtrate was concentrated in vacuo and the residue was purified by reverse-phase HPLC [Phenomenex Luna C18, 100×21.2 mm, 5-50% ACN/water containing 0.1% HOAc over 30 min; Flow: 20 mL/min]. The product-containing fraction was diluted with water, frozen, and lyophilized to afford 70 mg (52%) of 118.HOAc as a white-colored solid. 1H NMR (300 MHz, d6-DMSO), mixture of amide rotomers: δ9.72 (br s, 1H), 8.80 (d, J=8.1 Hz, 1H), 4.50 (m, 1H), 4.35 (m, 1H), 4.18 (app t, J=6.6 Hz, 1H), 3.99 (app t, J=9.3 Hz, 1H), 3.85 (app q, J=6.6 Hz, 1H), 3.75 (m, 1H), 3.36 (br s, 3H), 3.21 (m, 1H), 2.98 (m, 1H), 2.44 (s, 3H), 2.36 (m, 1H), 2.14 (m, 2H), 1.99 (m, 1H), 1.71-1.51 (m, 5H), 1.34 (d, J=6.9 Hz, 3H), 1.14-0.98 (m, 5H) ppm. 13C NMR (75 MHz, d6-DMSO), mixture of amide rotomers: δ169.5, 169.3, 61.9, 61.3, 56.4, 56.3, 46.9, 45.3, 31.6, 31.3, 29.4, 28.8, 26.3, 26.2, 26.0, 16.4 ppm. Mass spectrum, m/z [337.2] (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth (Celite®)
  2. washwashed with EtOAc and MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by reverse-phase HPLC [Phenomenex Luna C18, 100×21.2 mm, 5-50% ACN/water containing 0.1% HOAc over 30 min; Flow: 20 mL/min]
  5. additionThe product-containing fraction was diluted with water
  6. temperaturefrozen

Sources & evidence

ORD record
ord-cc4323c8e4274a8f9aeb12d349351089
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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