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Triethylamine → cis-Ethyl 4-(amino-5-chloro-2-methoxybenzoylamino)-3-methoxy-1-piperidinecarboxylate

HRID 1088399
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1088399
N[C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][CH3:13])[CH:3]=1.C(Cl)(=O)OCC.[NH2:20][C@H:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][C@H:22]1[O:32][CH3:33].C([N:36](CC)CC)C>ClC(Cl)Cl>[NH2:36][N:20]([C:6](=[O:8])[C:5]1[CH:9]=[C:10]([Cl:11])[CH:2]=[CH:3][C:4]=1[O:12][CH3:13])[C@H:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][C@H:22]1[O:32][CH3:33]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 13677746Ethyl cis-(4-amino-3-methoxypiperidino)formate

Produkt 1

HCID 131716645cis-Ethyl 4-(amino-5-chloro-2-methoxybenzoylamino)-3-methoxy-1-piperidinecarboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 22.5 parts of 4-amino-5-chloro-2-methoxybenzoic acid in 405 parts of trichloromethane were added dropwise successively 11.8 parts of N,N-diethylethanamine and 13 parts of ethyl carbonochloridate at a temperature below 10° C. Stirring was continued for 45 minutes at a temperature below 10° C. Then there was added dropwise a solution of 19.15 parts of cis-ethyl 4-amino-3-methoxy-1-piperidinecarboxylate in 360 parts of trichloromethane at the same temperature. Upon completion, stirring was continued for 18 hours at room temperature. The reaction mixture was washed successively three times with water, once, with a 5% sodium hydroxide solution and again twice with water. The organic phase was dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 29.3 parts (80%) of cis-ethyl 4-(amino-5-chloro-2-methoxybenzoylamino)-3-methoxy-1 -piperidinecarboxylate as a residue (compound 168).

Aufarbeitung

  1. stirringUpon completion, stirring
  2. waitwas continued for 18 hours at room temperature
  3. washThe reaction mixture was washed successively three times with water
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-9c15bfa3ea184a6fa8a3c5805cae205a
Quelldatensatz
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04962115

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