Dimethylformamide → HCID 23302093, compound

HRID 1952976Notes

Reaction equation

HRID 1952976 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[C:48]([CH3:51])([O-])[CH3:49].[K+].I[CH2:54][CH2:55][CH2:56][CH3:57].[CH3:58]N(C)C=O>C(OCC)(=O)C>[CH2:54]([N:25]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:24][CH2:23][CH2:22][N:21]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:12]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:11][CH2:10][CH2:9][N:8]([CH2:58][CH2:49][CH2:48][CH3:51])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:55][CH2:56][CH3:57]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10962Butyl iodideHCID 14585891HCID 14585891, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 23302093HCID 23302093, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 1,5,14,18-tetra(t-butoxycarbonyl)-1,5,14,18-tetraazaoctadecane (3.5 g, 0.0053 mol), prepared as in step C or example 1, with potassium t-butoxide (2.7 g, 0.024 mol) and 1-iodobutane (2.57 mL, 0.024 mol) in dimethylformamide (10 mL). Stir the reaction for 18 hours. Concentrate the reaction under vacuum (0.5 mm at 45° C.) and dissolve the residue in ethyl acetate (500 mL). Wash with water (2×100 mL), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (20% ethyl acetate/hexane, silica gel) to provide 1,18-bis-(butyl)-1,5,14,18-tetra(t-butoxycarbonyl)-1,5,14,18-tetraazaoctadecane (1.32 g), Rf =0.36 eluting with 20% ethyl acetate/hexane.

Workup

  1. customthe reaction for 18 hours
  2. concentrationConcentrate
  3. customthe reaction under vacuum (0.5 mm at 45° C.)
  4. washWash with water (2×100 mL)
  5. dry with materialdry over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the residue by flash chromatography (20% ethyl acetate/hexane, silica gel)

Sources & evidence

ORD record
ord-93d716d5b49d42acbbfa5c68aaac8d19
Source dataset
uspto-grants-2000_09
Patent number
US06114394

Reaction notes

Loading…