Methanol → HCID 18457526, compound

HRID 1272503Notes

Reaction equation

HRID 1272503 reaction equation
[C:1]([CH:5]1[NH:19][C:18](=[O:20])[CH:17]([CH2:21][N:22]([O:25]CC2C=CC=CC=2)[CH:23]=[O:24])[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]1=[O:33])([CH3:4])([CH3:3])[CH3:2].CO.[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([CH:5]1[NH:19][C:18](=[O:20])[CH:17]([CH2:21][N:22]([OH:25])[CH:23]=[O:24])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]1=[O:33])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 73010119HCID 73010119, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18457526HCID 18457526, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The cyclic compound 14 (50.0 mg) was dissolved in ethyl acetate and methanol (1:1, 10 mL) and 20 mg of 10% Pd/C as added. The mixture was exposed to 1 atm of hydrogen until all the starting material was consumed. The charcoal was removed by filtration and the filtrate was concentrated to give the desired compound quantitatively. 1H NMR (250 MHz, CDCl3) δ 9.39 (brs, 1H), 8.37 (brs, 0.27H),7.86 (brs, 0.73H), 7.40 (d, J=8.7 Hz, 0.27H), 6.94 (brs, 1H), 6.57 (brs, 0.73H), 4.33 (m, 1H) 3.81 (m, 2H), 3.43 (m, 1H), 2.87 (m, 2H), 1.64 (brs, 2H), 1.45–1.23 (m, 16H), 0.96 (s, 9H); 13C NMR (63 MHz, CDCl3) δ 175.0, 173.3, 171.2, 170.9, 157.2, 61.1, 60.4, 52.7, 44.5, 38.5, 34.6, 29.8, 28.0, 27.8, 27.5, 26.8, 26.5, 25.2, 21.1, 14.2. HRESI-MS: C19H35N3O4Na+ ([M+Na])+calc'd 392.2520, found 392.2504. HPLC analysis showed a purity of ˜96% (FIG. 1).

Workup

  1. customwas consumed
  2. customThe charcoal was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-608265d96ae549a6bc32c685634471d2
Source dataset
uspto-grants-2007_04
Patent number
US07208595B2

Reaction notes

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