Trifluoroacetic acid → (4-(1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)piperidin-4-yl)methanol

HRID 241649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241649
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]4([CH2:42][OH:43])[CH2:22][CH2:21][N:20](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH2:19][CH2:18]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:44][C:45]([CH3:48])([CH3:47])[CH3:46])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]4([CH2:42][OH:43])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:44][C:45]([CH3:48])([CH3:47])[CH3:46])[CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 58513617(4-(1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)-1-tritylpiperidin-4-yl)methanol

Produkt 1

HCID 58513575(4-(1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)piperidin-4-yl)methanolAusbeute 105,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (4-(1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)-1-tritylpiperidine-4-yl)methanol (STEP F, 300 mg, 0.453 mmol) in dichloromethane (6 mL) was trifluoroacetic acid (2 mL). After 20 min, the mixture was concentrated in vacuo and the residue was diluted with methanol and the solution was filtered through strong cationic exchange column (SCX). The column was washed with 1 mol/L ammonia methanol to wash out the product. The filtrate was concentrated in vacuo to give the title compound (200 mg, quantitative yield).

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. additionthe residue was diluted with methanol
  3. filtrationthe solution was filtered through strong cationic exchange column (SCX)
  4. washThe column was washed with 1 mol/L ammonia methanol
  5. washto wash out the product
  6. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0cce407ac2614684ba8867210ac08daa
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653063B2

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