Trityl chloride → HCID 13777646, compound

HRID 1522891Notes

Reaction equation

HRID 1522891 reaction equation
[CH2:1]([OH:5])[C@H:2]([OH:4])[CH3:3].[C:6](Cl)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl.CN(C1C=CC=CN=1)C>[CH3:33][S:34]([O:4][C@H:2]([CH3:3])[CH2:1][O:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:36])=[O:35]

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 259994R-(-)-1,2-Propanediol

Product 1

HCID 13777646HCID 13777646, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-propane-1,2-diol (2.82 g, 37.1 mmol) and trityl chloride (10.5 g, 37.7 mmol) in DCM (100 mL) at 0° C., dimethylaminopyridine (53 mg, 0.43 mmol) was added followed by dropwise addition of triethylamine (13.0 mL, 93.3 mmol). The solution was allowed to warm to room temperature, stirred overnight, and re-cooled to 0° C. Methanesulfonyl chloride (3.2 mL, 41.2 mmol) was added to the reaction, and the mixture was stirred for 4 h at 0° C. The reaction was quenched (50 mL 1N HCl), and the layers were separated. The organic phase was washed (50 mL 1N HCl and 50 mL brine), dried (Na2SO4) and concentrated under reduced pressure. The crude material was purified on a silica gel column to give (R)-1-(trityloxy)propan-2-yl methanesulfonate (13.1 g) as a thick oil which solidified over time. 1H NMR (DMSO-d6): δ 7.50-7.20 (m, 15H), 4.85 (m, 1H), 3.34 (s, 3H), 3.12 (m, 2H), 1.28 (d, 3H).

Workup

  1. temperaturere-cooled to 0° C
  2. stirringthe mixture was stirred for 4 h at 0° C
  3. customThe reaction was quenched (50 mL 1N HCl)
  4. customthe layers were separated
  5. washThe organic phase was washed (50 mL 1N HCl and 50 mL brine)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified on a silica gel column

Sources & evidence

ORD record
ord-8879f9f2db864042aa4dd341961b3d41
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

Loading…