Hydrochloric Acid → 6,12,18-Trihydroxy-7,13,19-trioxo-6,12,18-triazaeicosanamine hydrochloride

HRID 2380140Notes

Reaction equation

HRID 2380140 reaction equation
C([O:8][N:9]([C:16](=[O:48])[CH2:17][CH2:18][CH2:19][CH2:20][N:21]([O:40]CC1C=CC=CC=1)[C:22](=[O:39])[CH2:23][CH2:24][CH2:25][CH2:26][N:27]([O:31]CC1C=CC=CC=1)[C:28](=[O:30])[CH3:29])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])C1C=CC=CC=1.[ClH:49]>CO.[Pd]>[ClH:49].[OH:8][N:9]([C:16](=[O:48])[CH2:17][CH2:18][CH2:19][CH2:20][N:21]([OH:40])[C:22](=[O:39])[CH2:23][CH2:24][CH2:25][CH2:26][N:27]([OH:31])[C:28](=[O:30])[CH3:29])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 101008386,12,18-Tris(benzyloxy)-7,13,19-trioxo-6,12,18-triazaeicosanenitrile

Product 1

HCID 189566666,12,18-Trihydroxy-7,13,19-trioxo-6,12,18-triazaeicosanamine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound (9) (1.000 g, 1,522 mmol) was dissolved in CH3OH (210 mL), followed by addition of 0.1N HCl (from concentrated HCl and methanol, 16.75 mL, 1.675 mmol) and 10% Pd-C (0.6 g). The mixture was stirred under H2 (1 atm) at room temperature overnight. The catalyst was filtered and the solvent was removed. The residue was purified by Sephadex LH-20 column chromatography, eluting with 15% MeOH/toluene, to generate 560 mg (86%) of [A] as a colorless solid: NMR (CD3OD) δ 1.30-1.97 (m, 14H), 2.17 (s, 3H), 2.60 (t, 4H, J=6), 3.00 (t, 2H, J=6), 3.70 (t, 6H, J=6). Anal. (C17H35ClN4O6) C, H, N.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was removed
  3. customThe residue was purified by Sephadex
  4. washcolumn chromatography, eluting with 15% MeOH/toluene

Sources & evidence

ORD record
ord-701b97b6d9ed4385a594bdf969934574
Source dataset
uspto-grants-1994_11
Patent number
US05364965

Reaction notes

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