Triethylamine → HCID 11053544, compound

HRID 993028Notes

Reaction equation

HRID 993028 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].C(N(CC)CC)C.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][O:8][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:23])[NH2:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 11053544HCID 11053544, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

L-Serine methyl ester hydrochloride (7.09 g) was suspended in dichloromethane (100 mL), and to the suspension 4-(dimethylamino)pyridine (700 mg) and triethylamine (9.69 g) were added, and tert-butyldimethylchlorosilane (7.0 g) were added portionwise at 0° C. to the mixture to conduct stirring at room temperature. The reaction mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=20:1) to obtain the title compound.

Workup

  1. washThe reaction mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-4b7af7016cfa424595af1ff75c48dc34
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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