Chloroacetyl chloride → tert-butyl (2S)-2-(2-chloroacetamido)-3-phenylpropanoate

HRID 77515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77515
Cl.[C:2]([O:6][C:7](=[O:17])[C@@H:8]([NH2:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[Cl:25][CH2:26][C:27](Cl)=[O:28]>ClCCl.O>[C:2]([O:6][C:7](=[O:17])[C@@H:8]([NH:16][C:27](=[O:28])[CH2:26][Cl:25])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Komponenten

6

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)

Produkt 1

HCID 86713545tert-butyl (2S)-2-(2-chloroacetamido)-3-phenylpropanoateAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 3.0 g (11.6 mmol) (S)-2-amino-3-phenyl-propionic acid tert-butyl ester hydrochloride (Aldrich) and 3.32 mL (23.9 mmol) triethylamine (Aldrich) in dichloromethane (30 mL), 0.97 mL (12.2 mmol) chloroacetyl chloride (Aldrich) is added dropwise and the resulting mixture is stirred at room temperature for 4 h. The reaction mixture is diluted with water (25 mL), the organic layer is separated, washed with 10% NaHCO3 solution (25 mL), dried (MgSO4) and finally evaporated under reduced pressure to yield the title compound (3.4 g).

Aufarbeitung

  1. additionis added dropwise
  2. customthe organic layer is separated
  3. washwashed with 10% NaHCO3 solution (25 mL)
  4. dry with materialdried (MgSO4)
  5. customfinally evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-45ac19933d4f45b99cbb5458dd73736d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841309B2

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