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Citric Acid → N-(tert-butoxycarbonyl)-2-aminoethanethiol

HRID 1461470
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1461470
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][S:11]SCCN)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][SH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 22245556tert-butyl N-(2-((2-aminoethyl)disulfanyl)ethyl)carbamate

Produkt 1

HCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiolAusbeute 106,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of bis N-(t-butyloxycarbonyl)-cystamine (77.37 g, 0.220 mole) from Example 1, in 1 L of ethanol was treated with NaBH4 (32.5 g, 0.859 mmole). Vigorous gas evolution ensued and subsided in 40 minutes. The reaction was stirred for an additional half hour and was poured into 2.5 L of a cold dilute solution of citric acid (pH 6). The mixture was then extracted with 3×1 L of chloroform. The combined organic extracts were dried with MgSO4 and the solvents were removed under reduced pressure. The resulting residue was distilled (66°-73° C. 0.25 torr) to obtain the product (41.5 g, 53% yield).

Aufarbeitung

  1. extractionThe mixture was then extracted with 3×1 L of chloroform
  2. dry with materialThe combined organic extracts were dried with MgSO4
  3. customthe solvents were removed under reduced pressure
  4. distillationThe resulting residue was distilled (66°-73° C. 0.25 torr)

Quellen und Nachweise

ORD-Eintrag
ord-7311b23c74dc40e28c313817a301885f
Quelldatensatz
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05075440

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