Trityl chloride → 3-Tetradecylthioacetylamino-1-triphenylmethyloxypropan-2-ol

HRID 853203Notes

Reaction equation

HRID 853203 reaction equation
Cl[C:2]([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:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:21]([CH2:35][C:36]([NH:38][CH2:39][CH:40]([OH:43])[CH2:41][OH:42])=[S:37])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>N1C=CC=CC=1>[CH2:21]([CH2:35][C:36]([NH:38][CH2:39][CH:40]([OH:43])[CH2:41][O:42][C:2]([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:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[S:37])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 866032113-Tetradecylthioacetylaminopropane-1,2-diol

Product 1

HCID 866032103-Tetradecylthioacetylamino-1-triphenylmethyloxypropan-2-olYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

Chlorotriphenylmethane (2.833 g, 10.16 mmol) was added to a solution of 3-tetradecylthioacetylaminopropane-1,2-diol (example 2) (3 g, 8.30 mmol) in pyridine (2.5 ml). The reaction mixture was stirred at 50° C. for 24 hours and the solvent was then vacuum evaporated. The residue was taken up in water and extracted with dichloromethane. The organic phase was washed with 1 N aqueous hydrochloric acid then with an aqueous solution saturated in sodium chloride. It was dried on magnesium sulfate, filtered and the solvent was evaporated. The residue obtained (6.36 g) was purified by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 98:2) to give the desired compound in the form of a white powder.

Workup

  1. customvacuum evaporated
  2. extractionextracted with dichloromethane
  3. washThe organic phase was washed with 1 N aqueous hydrochloric acid
  4. customIt was dried on magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue obtained (6.36 g)
  8. customwas purified by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 98:2)

Sources & evidence

ORD record
ord-8ae791455841494f8bd3143af1f11fad
Source dataset
uspto-grants-2007_08
Patent number
US07253296B2

Reaction notes

Loading…