HCID 91210435, compound → HCID 69030403, compound

HRID 2112566Notes

Reaction equation

HRID 2112566 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][O:7][C@@H:8]1[C@@H:16]([O:17][CH2:18][CH2:19][CH2:20][N:21]=[N+]=[N-])[C@@H:15]([O:24][CH2:25][CH2:26][CH2:27][N:28]=[N+]=[N-])[C@@H:14]([CH2:31][O:32][CH2:33][CH2:34][CH2:35][N:36]=[N+]=[N-])[O:13][C@@H:9]1[O:10][CH2:11][CH3:12])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH2:5][CH2:6][O:7][C@@H:8]1[C@@H:16]([O:17][CH2:18][CH2:19][CH2:20][NH2:21])[C@@H:15]([O:24][CH2:25][CH2:26][CH2:27][NH2:28])[C@@H:14]([CH2:31][O:32][CH2:33][CH2:34][CH2:35][NH2:36])[O:13][C@@H:9]1[O:10][CH2:11][CH3:12]

Participants

4

Reactant 1

HCID 91210435HCID 91210435, compound

Product 1

HCID 69030403HCID 69030403, compoundYield 107.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Azide 5 (61.0 mg, 0.11 mmol) was hydrogenated with Pd/C (10%, 10 mg) in methanol (5 mL) overnight at room temperature. The mixture was filtered through a bed of CELITE, and the filtrate was then concentrated to give tetraamine 6 (51.5 mg, 100%); 1H-NMR (D2O): δ5.10 (d, 1H, J=3.4 Hz, H-1), 4.06-3.98 (m, 1H, OCHHCH2CH2NH2), 3.96-3.92 (m, 1H, H-4), 3.90˜3.48 (m, 14H, H-2, H-3, H-5, H-6, H-6′, OCH2CH2CH2NH2, and OCH2CH3), 2.89-2.70 (m, 8H, OCH2CH2CH2NH2), 1.90-1.65 (m, 8H, OCH2CH2CH2NH2), 1.18 (t, 3H, J=7.1 Hz, OCH2CH3); ES-MS: 437.48 (M+H)+, 219.16 (M+2H)2+.

Workup

  1. filtrationThe mixture was filtered through a bed of CELITE
  2. concentrationthe filtrate was then concentrated

Sources & evidence

ORD record
ord-0c5f849d3e3d4590a65472642f598e9a
Source dataset
uspto-grants-2009_04
Patent number
US07524821B2

Reaction notes

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