Methanol → HCID 18457526, compound

HRID 493898Notes

Reaction equation

HRID 493898 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]+), callc'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-afe92c37a687431f88f7a7ccc51c6a86
Source dataset
uspto-grants-2009_05
Patent number
US07538085B2

Reaction notes

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