Trifluoroacetic acid → Trifluoroacetic acid

HRID 338640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338640
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([CH3:56])([CH3:55])[C@H:13]3[C@:26]([CH3:29])([CH2:27][CH:28]=2)[C@@H:25]2[C@:16]([CH3:54])([C@@:17]4([CH3:53])[C@H:22]([CH2:23][CH2:24]2)[C@H:21]2[C@H:30]([C:33]([CH3:35])=[CH2:34])[CH2:31][CH2:32][C@:20]2([NH:36][CH2:37][CH2:38][N:39]2[CH2:44][C@@H:43]5[CH2:45][C@H:40]2[CH2:41][N:42]5C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)[CH2:15][CH2:14]3)=[CH:7][CH:6]=1)=[O:4].[C:57]([OH:63])([C:59]([F:62])([F:61])[F:60])=[O:58]>C(Cl)Cl>[C@H:40]12[CH2:45][C@H:43]([NH:42][CH2:41]1)[CH2:44][N:39]2[CH2:38][CH2:37][NH:36][C@:20]12[CH2:32][CH2:31][C@@H:30]([C:33]([CH3:35])=[CH2:34])[C@@H:21]1[C@@H:22]1[C@@:17]([CH3:53])([CH2:18][CH2:19]2)[C@@:16]2([CH3:54])[C@@H:25]([C@:26]3([CH3:29])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:55])([CH3:56])[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)=[CH:28][CH2:27]3)[CH2:24][CH2:23]1.[C:57]([OH:63])([C:59]([F:62])([F:61])[F:60])=[O:58]

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86701804HCID 86701804, Verbindung

Produkt 2

HCID 6422Trifluoroacetic acidAusbeute 121 %HCID 86701803HCID 86701803, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (1S,4S)-tert-butyl 5-(2-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(methoxycarbonyl)phenyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-3a-yl)amino)ethyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (419 mg, 0.545 mmol) in DCM (10 mL) was added TFA (2 mL, 26.0 mmol) and the mixture was stirred at rt for 3 h. The reaction mixture was concentrated and dark brown viscous oil was dried to remove all TFA. The material was purified by reverse phase HPLC using HPLC method 6 and dried under vacuum to give methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate, 3 TFA (75.2 mg, 12.28% yield) as a light brown solid. LC/MS: m/e 668.7 (M+H)+, 2.36 min (method 3). 1H NMR (400 MHz, CHLOROFORM-d) δ 9.77 (br. s., 1H), 9.49 (br. s., 1H), 7.92 (d, J=8.1 Hz, 2H), 7.19 (d, J=8.1 Hz, 2H), 5.28 (d, J=4.4 Hz, 1H), 4.76 (br. s., 1H), 4.69 (br. s., 1H), 4.31 (br. s., 1H), 3.96 (br. s., 1H), 3.90 (s, 3H), 3.66 (br. s., 1H), 3.40-3.10 (m, 5H), 3.09-2.89 (m, 2H), 2.81 (br. s., 1H), 2.23-2.06 (m, 4H), 2.05-1.91 (m, 3H), 1.85 (br. s., 1H), 1.78-1.73 (m, 1H), 1.69 (br. s., 3H), 1.65 (br. s., 1H), 1.62-1.30 (m, 11H), 1.26-1.17 (m, 2H), 1.11 (br. s., 3H), 1.05 (br. s., 3H), 0.99 (br. s., 3H), 0.93 (br. s., 6H). 13C NMR (101 MHz, CHLOROFORM-d) 167.2, 148.5, 147.1, 146.2, 130.0, 128.5, 127.9, 123.8, 114.8, 111.6, 77.24-77.18, 71.3, 65.8, 60.9, 57.7, 54.4, 52.7, 52.0, 49.2, 48.7, 48.62-48.49, 46.3, 45.0, 42.0, 41.6, 40.6, 37.4, 37.0, 36.2, 33.6, 32.5, 29.4, 28.0, 27.3, 25.8, 25.0, 20.9, 20.8, 19.5, 19.1, 16.3, 15.9, 15.2, 14.4.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customdark brown viscous oil was dried
  3. customto remove all TFA
  4. customThe material was purified by reverse phase
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-49d4196d23a24069a021a516039f0981
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889854B2

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