4-Toluenesulfonyl chloride → cis-N-Carbobenzyloxy-4-tosyloxy-L-proline, methyl ester

HRID 1733350

Reaktionsgleichung

Reaktionsgleichung von HRID 1733350
[C:1]([N:11]1[CH2:19][C@@H:18]([OH:20])[CH2:17][C@H:12]1[C:13]([O:15][CH3:16])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>N1C=CC=CC=1>[C:1]([N:11]1[CH2:19][C@@H:18]([O:20][S:21]([C:24]2[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:17][C@H:12]1[C:13]([O:15][CH3:16])=[O:14])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 688413(2S,4S)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 14036189cis-N-Carbobenzyloxy-4-tosyloxy-L-proline, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Following the procedure of Example 19(b), the methyl ester product from part (b) is treated with 12.4 g. of tosyl chloride in 45 ml. of pyridine to give 13.2 g. of cream-colored product; m.p. 114°-117° (s. 105°). 13 g. of this material are recrystallized from 70 ml. of ethanol to 8.4 g. of colorless cis-N-carbobenzyloxy-4-tosyloxy-L-proline, methyl ester; m.p. 133°-135°; [α]D25 -26° (c=1%, chloroform).

Aufarbeitung

  1. customm.p. 114°-117° (s. 105°)
  2. customof this material are recrystallized from 70 ml

Quellen und Nachweise

ORD-Eintrag
ord-291d7a927ed04c2781925f8e6d809f78
Quelldatensatz
uspto-grants-1980_12
Patentnummer
US04241076

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