Triethylamine → HCID 86618885, compound

HRID 252408Notes

Reaction equation

HRID 252408 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][CH:10]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:11][CH:12]([CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[C:20]([O:27][CH2:28][CH2:29][O:30][CH3:31])[CH:21]=[CH:22][CH:23]=2)[CH:18]=1)[CH:13]([CH3:15])[CH3:14]>ClCCl>[CH:9]([CH:10]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:38])[CH3:37])[CH2:11][CH:12]([CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[C:20]([O:27][CH2:28][CH2:29][O:30][CH3:31])[CH:21]=[CH:22][CH:23]=2)[CH:18]=1)[CH:13]([CH3:15])[CH3:14])=[O:8]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86618886HCID 86618886, compound

Product 1

HCID 86618885HCID 86618885, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.04 ml of triethylamine and then a solution of 1.31 g of sulphur trioxide-pyridine complex are added at 0° C. to the solution of 0.86 g of tert-butyl {1-hydroxymethyl-3-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-4-methylpentyl}carbamate in 8 ml of dichloromethane. After 45 minutes, the reaction mixture is admixed cautiously with ice-water. The resulting mixture is poured onto 1N HCl/ice and extracted with ethyl acetate (3×). The combined organic phases are washed successively with water (2×) and brine, clarified by filtration through Hyflo®, dried over sodium sulphate and concentrated by evaporation. In this way, the crude title compound is obtained.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic phases are washed successively with water (2×) and brine
  3. filtrationclarified by filtration through Hyflo®
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2c4cddd044754287a088b3b4e3d77a6d
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

Loading…