Trityl chloride → N-(Triphenylmethyl)-L-serine methyl ester

HRID 1663448Notes

Reaction equation

HRID 1663448 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.Cl.[CH3:22][O:23][C:24](=[O:29])[C@H:25]([CH2:27][OH:28])[NH2:26].C(N(CC)CC)C>ClCCl>[C:2]([NH:26][C@H:25]([C:24]([O:23][CH3:22])=[O:29])[CH2:27][OH:28])([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

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 7128367N-(Triphenylmethyl)-L-serine methyl esterYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chlorotriphenylmethane (265 g, 950 mmol) dissolved in 750 mL of dichloromethane was added dropwise to a stirred solution of L-serine methyl ester hydrochloride (148 g, 950 mmol) and triethylamine (260 mL, 1900 mmol) in 1.5 L of CH2Cl2 at 0° C. The cloudy yellow solution was stirred for 18 hours at ambient temperature. The reaction mixture was filtered to remove solids and the filtrate was washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give a yellow oil. The oil was concentrated from acetonitrile and then stirred in hexanes until a precipitate formed. The resulting solid was filtered to afford 310 g of methyl N-trityl-L-serinate as an off white powder.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove solids
  3. washthe filtrate was washed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow oil
  8. concentrationThe oil was concentrated from acetonitrile
  9. stirringstirred in hexanes until a precipitate
  10. customformed
  11. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-7960514397444f5694d1e63cd0eeb7ae
Source dataset
uspto-grants-2011_10
Patent number
US08034938B2

Reaction notes

Loading…