Methyl chloroacetate → N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyrosine

HRID 1633274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633274
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:22][C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-

Produkt 1

HCID 59910020N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyrosineAusbeute 135,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of diphenylmethyl ester of N-tert-butoxycarbonyl-L-tyrosine (5.00 g), methyl chloroacetate (1.45 g) and potassium carbonate (1.85 g) in N,N-dimethylformamide (75 ml) was stirred for 20 hours at room temperature. The mixture was diluted with water (100 ml) and extracted with ethyl acetate. The extract was washed with diluted hydrochloric acid, aqueous sodium bicarbonate, and then brine. After dried over magnesium sulfate, the extract was evaporated to dryness to give diphenylmethyl ester of N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyrosine (6.40 g), mp. 69°-73° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with diluted hydrochloric acid, aqueous sodium bicarbonate
  3. dry with materialAfter dried over magnesium sulfate
  4. customthe extract was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9bd3fbb4db004d4b9b55a4e9cdbe2aee
Quelldatensatz
uspto-grants-1984_10
Patentnummer
US04479942

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