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4-(4-Benzyloxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid → 1-benzyl-4-(4-(benzyloxy)phenylsulfonyl)-N-hydroxypiperidine-4-carboxamide

HRID 1595649
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1595649
C([O:3][C:4]([C:6]1([S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=O)C.C(OC1C=CC(S(C2(C(O)=O)CCN(CC3C=CC=CC=3)CC2)(=O)=O)=CC=1)C1C=CC=CC=1.[OH:69][NH:70]C(C1CCN(CC2C=CC=CC=2)C(S(C2C=CC(OCC3C=CC=CC=3)=CC=2)(=O)=O)C1)=O>CO.C1COCC1>[OH:69][NH:70][C:4]([C:6]1([S:19]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:27]=2)(=[O:21])=[O:20])[CH2:7][CH2:8][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][CH2:11]1)=[O:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 109726574-(4-Benzyloxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acidHCID 11123863HCID 11123863, VerbindungHCID 86757373HCID 86757373, Verbindung

Produkt 1

HCID 99130531-benzyl-4-(4-(benzyloxy)phenylsulfonyl)-N-hydroxypiperidine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815
MeOH tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

4-(4-Benzyloxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid ethyl ester (5.0 g, 10.1 mmol) was dissolved in MeOH/THF (1:1, 200 ml) and stirred at room temperature for 72 hrs. At the end reaction mixture was concentrated and the product was nuetralised with con. HCl by dissolving it in water (200 mL). After the neutralization reaction mixture was concentrated to dryness. Ice cold water (100 mL) was added to the solid and filtered. The product 4-(4-Benzyloxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid was dried at 50° C. and taken to next step with out any purification. Colorless solid. MP: 66-68; Yield: 4.3 g, 91% ; MS: 466 (M+H) Starting from 4-(4-Benzyloxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid (4.65 g, 10.0 mmol) and following the procedure outlined in example 83, 1.1 g of 4-(4-Benzyloxy-benzenesulfonyl-1-benzyl-piperidine-4-carboxylic acid hydroxyamide was isolated as a colurless solid. Yield 21%; mp 89° C.; MS: 481.1 1H NMR (300 MHz, DMSO-d6): δ2.27 (m, 3H), 2.76-2.79 (m, 2H), 3.43 (m, 4H),4.30 (s, 2H), 7.14-7.17 (d,2H), 7.50-7.73 (m, 5H), 9.37 (s, 1H), 10.53 (s, 1H), 11.18 (s, 1H).

Aufarbeitung

  1. customAt the end reaction mixture
  2. concentrationwas concentrated
  3. dissolutionHCl by dissolving it in water (200 mL)
  4. customAfter the neutralization reaction mixture
  5. concentrationwas concentrated to dryness
  6. additionIce cold water (100 mL) was added to the solid
  7. filtrationfiltered
  8. dry with materialThe product 4-(4-Benzyloxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid was dried at 50° C.
  9. customtaken to next step with out any purification
  10. customwas isolated as a colurless solid

Quellen und Nachweise

ORD-Eintrag
ord-a817b1226efd464db84d6d0d512d9652
Quelldatensatz
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06288086B1

Notizen zur Reaktion

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