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L-Serine → (2S)-3-Hydroxy-2-[(triphenylmethyl)amino]propanoic acid

HRID 80323
Notes
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Reaction equation

HRID 80323 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].C[Si](Cl)(C)C.C(N(CC)CC)C.[C:20]1([C:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)Cl)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl.CO>[C:20]1([C:26]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5951L-SerineHCID 6397ChlorotrimethylsilaneHCID 6456Trityl chlorideHCID 8471Triethylamine2×

Product 1

HCID 10991634(2S)-3-Hydroxy-2-[(triphenylmethyl)amino]propanoic acidYield 5.2%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
2×
HCID 6344DichloromethaneSolvent

Procedure

L-Serine (2.10 g, 20.0 mmol) (Wako Pure Chemical Industries, Ltd.) was dissolved in methylene chloride (20 mL) (Wako Pure Chemical Industries, Ltd.), and then trimethylsilyl chloride (8.9 mL) (Shin-Etsu Chemical Co., Ltd.) was added thereto, followed by reflux for 20 minutes. The mixture was returned to room temperature, and then triethylamine (10 mL) (Wako Pure Chemical Industries, Ltd.) was added thereto, followed by reflux for 45 minutes. The mixture was ice-cooled, and then triethylamine (2.8 mL) (Wako Pure Chemical Industries, Ltd.) and triphenylchloromethane (5.61 g, 20.1 mmol) (Wako Pure Chemical Industries, Ltd.) were added thereto, followed by stirring at room temperature for 5 hours. An excessive amount of methanol (Wako Pure Chemical Industries, Ltd.) was added to the reaction solution, and the mixture was concentrated under reduced pressure. The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.):methanol (Wako Pure Chemical Industries, Ltd.)=99:1 as an eluent), to thereby obtain the title compound (0.36 g, 5% yield).

Workup

  1. temperatureby reflux for 20 minutes
  2. customwas returned to room temperature
  3. temperatureby reflux for 45 minutes
  4. temperaturecooled
  5. concentrationthe mixture was concentrated under reduced pressure
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b916d736b4584acab21f7f7a32f08400
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846012B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes