Benzyloxycarbonylglycine → Benzyloxycarbonylaminoacetyl chloride

HRID 258764

Reaktionsgleichung

Reaktionsgleichung von HRID 258764
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:17]>C(OCC)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([Cl:17])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 14349BenzyloxycarbonylglycineHCID 24819Phosphorus pentachloride

Produkt 1

HCID 12239759Benzyloxycarbonylaminoacetyl chlorideAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A stirred mixture of N-benzyloxycarbonylglycine [30 g.; prepared as described in Ber., 65, 1192, (1932)] and dry diethyl ether (190 ml.) was treated at 0° C. with phosphorus pentachloride (32 g.) during 5 minutes. The mixture was stirred at between 0° and 5° C. for a further 20 minutes and the solution was then filtered and the filtrate was evaporated. The residue was triturated with petrol (b.p. 40°-60° C.) and the petrol layer was decanted off, and this procedure was repeated several times, keeping the temperature below 20° C. throughout. A solid formed, which was filtered off to give N-benzyloxycarbonylglycyl chloride (25 g.), which was used immediately in the next stage. N-Benzyloxycarbonylglycyl chloride (13.0 g.) was added in one portion to a stirred solution of 4-amino-3-(3-methoxycarbonyl-2-thioureido)diphenyl thioether (10.0 g.; prepared as hereinbefore described in Example 2) in dry dimethylformamide. The temperature of the mixture rose to 35° C., and the stirring was continued for 20 minutes. The solution was then poured into water. The resulting oil solidified on scratching. The solid was filtered off and recrystallised from a mixture of dimethylformamide and methanol to give 4-(2-benzyloxycarbonylaminoacetamido)-3-(3-methoxycarbonyl-2-thioureido)diphenyl thioether (13.0 g.), m.p. 184°-186° C.

Aufarbeitung

  1. filtrationthe solution was then filtered
  2. customthe filtrate was evaporated
  3. customThe residue was triturated with petrol (b.p. 40°-60° C.)
  4. customthe petrol layer was decanted off
  5. customthe temperature below 20° C.
  6. customA solid formed
  7. filtrationwhich was filtered off

Quellen und Nachweise

ORD-Eintrag
ord-7de60ff1800a4e83b8420e88af8b3be9
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04034107

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