Trityl chloride → 4465-44-5

HRID 2197267Notes

Reaction equation

HRID 2197267 reaction equation
CCN(CC)CC.Cl.[CH3:9][O:10][C:11](=[O:16])[C@H:12]([CH2:14][OH:15])[NH2:13].[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[CH3:9][O:10][C:11](=[O:16])[CH:12]([NH:13][C:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:14][OH:15]

Participants

5

Reactant 3

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

Product 1

HCID 2790184465-44-5Yield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Et3N (13.4 mL, 96.78 mmol) in CH2Cl2 (40 mL) was added to a solution of L-serine methyl ester hydrochloride (5.0 g, 32.26 mmol) and Ph3CCl (13.5 g, 48.39 mmol) in CH2Cl2 (129 mL) at 0° C. under N2 atmosphere. The reaction was then allowed to warm to room temperature and was stirred overnight. The reaction was quenched with saturated NaHCO3, the aqueous layer was extracted with CH2Cl2, and the combined organic layers were washed with brine, dried and concentrated, the residue was purified by silica gel column chromatography which gave the title compound as a colourless solid (11.41 g, 98%).

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. washthe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel column chromatography which

Sources & evidence

ORD record
ord-33e2b5ce75834d16b346bd79ed290559
Source dataset
uspto-grants-2012_12
Patent number
US08338471B2

Reaction notes

Loading…