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

HRID 2380142Notes

Reaction equation

HRID 2380142 reaction equation
C([O:8][N:9]([C:16](=[O:56])[CH2:17][CH2:18][CH2:19][CH2:20][N:21]([O:48]CC1C=CC=CC=1)[C:22](=[O:47])[CH2:23][CH2:24][CH2:25][CH2:26][N:27]([O:39]CC1C=CC=CC=1)[C:28](=[O:38])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])C1C=CC=CC=1.[ClH:57]>CO.[Pd]>[ClH:57].[OH:8][N:9]([C:16](=[O:56])[CH2:17][CH2:18][CH2:19][CH2:20][N:21]([OH:48])[C:22](=[O:47])[CH2:23][CH2:24][CH2:25][CH2:26][N:27]([OH:39])[C:28](=[O:38])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 104177206,12,18-Tris(benzyloxy)-7,13,19-trioxo-6,12,18-triazaoctacosanenitrile

Product 1

HCID 189566656,12,18-Trihydroxy-7,13,19-trioxo-6,12,18-triazaoctacosanamine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound (10) (1.13 g, 1.47 mmol) was hydrogenated in CH3OH (150 mL) and 0.1N HCl (16.2 mL, 1.62 mmol) with 10% Pd-C (0.6 g) by the procedure used for [A]. Purification by Sephadex LH-20 column chromatography with 20% EtOH/toluene as the eluant produced 0.508 g (64%) of [A] as a colorless solid: NMR (CD3OD) δ 0.90 (t, 3H, J=6), 1.17-1.87 (m, 28H), 2.33-2.63 (m, 6H), 2.92 (t, 2H, J=6), 3.60 (t, 6H, J=6). Anal. (C25H51ClN4O6) C, H, N.

Workup

  1. customPurification by Sephadex
  2. customcolumn chromatography with 20% EtOH/toluene as the eluant produced 0.508 g (64%) of [A] as a colorless solid

Sources & evidence

ORD record
ord-f3caec430c7843e7b177df396ecd24e9
Source dataset
uspto-grants-1994_11
Patent number
US05364965

Reaction notes

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