Trityl chloride → 4465-44-5

HRID 910415Notes

Reaction equation

HRID 910415 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-295320d990cb4078937658895d0c9c43
Source dataset
uspto-grants-2011_09
Patent number
US08022092B2

Reaction notes

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