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Trifluoroacetic acid → HCID 131727015, Verbindung

HRID 29171
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 29171
[C:1]1([CH3:10])[C:2]([C:7](Cl)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH2:11][C@@H:12]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C@H:13]([OH:33])[CH2:14][N:15](OC1CCCC1)[S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)(=[O:18])=[O:17].F[C:42](F)(F)[C:43]([OH:45])=O.[CH:48](N(CC)C(C)C)([CH3:50])[CH3:49]>ClCCl>[CH2:34]([C@H:12]([NH:11][C:7](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:10])[C@@H:13]([OH:33])[CH:14]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)(=[O:17])=[O:18])[O:45][CH:43]1[CH2:42][CH2:50][CH2:48][CH2:49]1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 702762-Methylbenzoyl chlorideHCID 81531DiisopropylethylamineHCID 57010648N1-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N1-(cyclopentyloxy)-4-methoxy-1-benzenesulfonamide

Produkt 1

HCID 131727015HCID 131727015, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

o-Toluoyl chloride (7.8 μL, 0.0602 mmol) was added to a solution of N1-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N1-(cyclopentyloxy)-4-methoxy-1-benzenesulfonamide×trifluoracetic acid (Step 1, Example 48), (30 mg, 0.055 mmol) and N,N-diisopropylethylamine (23.8 μL, 0.137 mmol) in approximately 1.5 mL of dichloromethane under Argon. After stirring for 18 hours at ambient temperature, the reaction solvent was removed in vacuo and the residue was purified on a preparative TLC plate (20×20 cm, 500 μM) eluting with 96:4 methylene chloride:methanol. The product band was removed, eluted with 4:1 methylene chloride:methanol, filtered, and evaporated in vacuo. The residue was triturated from diethylether and hexane and the solvents were evaporated in vacuo to provide N1-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(4-methoxyphenyl)sulfonyl]amino-2-hydroxypropyl)-2-methylbenzamide (27 mg, 89%) as a solid. H1-NMR (dimethylsulfoxide-D6): 1.75 (m, 8H), 1.87 (s, 3H), 2.63 (m, 1H), 2.79 (bm, 1H), 3.05 (bm, 1H), 3.21 (bm, 1H), 3.69 (bm, 1H), 3.86 (s, 3H), 4.13 (bm, 1H), 4.86 (bm, 1H), 5.28 (bs, 1H), 6.79 (m, 1H), 7.21 (m, 10H), 7.72 (d, 2H), 8.06 (d, 1H). MS(ESI): 575(M+Na).

Aufarbeitung

  1. customthe reaction solvent was removed in vacuo
  2. customthe residue was purified on a preparative TLC plate (20×20 cm, 500 μM)
  3. washeluting with 96:4 methylene chloride
  4. customThe product band was removed
  5. washeluted with 4:1 methylene chloride
  6. filtrationmethanol, filtered
  7. customevaporated in vacuo
  8. customThe residue was triturated from diethylether and hexane
  9. customthe solvents were evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d950ddd320ca4e63a25573cca25af9f8
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07419967B2

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