Hydrogen Sulfide → 2-Amino-2-benzyloxymethyl-1-phthalimido-ethane

HRID 1614513

Reaktionsgleichung

Reaktionsgleichung von HRID 1614513
[CH2:1]([O:8][CH2:9][CH:10]([N:23]=[N+]=[N-])[CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.O.S>C(O)(=O)C>[NH2:23][CH:10]([CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:11][N:12]1[C:13](=[O:22])[C:14]2=[CH:21][CH:20]=[CH:19][CH:18]=[C:15]2[C:16]1=[O:17]

Komponenten

5

Edukt 3

HCID 402Hydrogen SulfideHCID 194385322-Benzyloxymethyl-2-azido-1-phthalimido-ethaneHCID 66926435Pyridine water

Produkt 1

HCID 194385522-Amino-2-benzyloxymethyl-1-phthalimido-ethaneAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Into a stirred solution of 2-benzyloxymethyl-2-azido-1-phthalimido-ethane (500 mg, 1.5 mmol) in 4:1 pyridine/water (25 ml) was bubbled hydrogen sulphide, and the reaction was monitored by TLC. After 4 hours, the gas flow was stopped, and the reaction flask sealed. The intense green reaction mixture was stirred for another 17 hours. TLC indicated full conversion of the starting material. Glacial acetic acid was added to pH 7, and the reaction mixture was evaporated to dryness in vacuo. After evaporation from ethanol (3×25 ml), the resulting brown solid was purified by chromatography. Yield=20%. The structure was confirmed by NMR and IR.

Aufarbeitung

  1. customthe reaction flask sealed
  2. customthe reaction mixture was evaporated to dryness in vacuo
  3. customAfter evaporation from ethanol (3×25 ml)
  4. customthe resulting brown solid was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-54a2dcf0bd174ba5a3ad293f2af038dd
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05198208

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