Trityl chloride → HCID 23292291, compound

HRID 365496Notes

Reaction equation

HRID 365496 reaction equation
C(N(CC)CC)C.[C:8](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)(=O)/C=C/C(O)=O.[CH2:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][CH2:38][CH:37]1[CH2:46][CH:47]1[CH2:51][NH:50][CH:49]=[N:48]1>C1C=CC=CC=1>[CH2:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][CH2:38][CH:37]1[CH2:46][CH:47]1[CH2:51][N:50]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:49]=[N:48]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178420883HCID 178420883, compound

Product 1

HCID 23292291HCID 23292291, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
20 °C

Procedure

1.25 ml (9 mmol) of triethylamine and 2.36 g (8.50 mmol) of trityl chloride are added, in succession, at 20° C., to a solution of the compound obtained in Example 16 (Step 4) in the form of the free amine (1.80 g, 8.40 mmol) in 50 ml of benzene, under nitrogen. After stirring for 15 hours at 20° C., the mixture is washed with H2O, and the organic phase is dried and concentrated in vacuo to yield an oily residue. Chromatography on a chiral column, eluting with a solution of triethylamine in toluene (0.5%), allows the 4 isomers to be separated in the form of white solids.

Workup

  1. washthe mixture is washed with H2O
  2. customthe organic phase is dried
  3. concentrationconcentrated in vacuo
  4. customto yield an oily residue
  5. washChromatography on a chiral column, eluting with a solution of triethylamine in toluene (0.5%)
  6. customto be separated in the form of white solids

Sources & evidence

ORD record
ord-b75a4999e9ba433eab964cc510f705e8
Source dataset
uspto-grants-2000_10
Patent number
US06127396

Reaction notes

Loading…