Diisopropylethylamine → 2-(trimethylsilyl)ethyl (S)-2-(3-benzoylcyclohexanecarboxamido)-3-cyclohexylpropylmethylcarbamate

HRID 1254239

Reaktionsgleichung

Reaktionsgleichung von HRID 1254239
[C:1]([C@@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([OH:17])=O)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][C@@H:19]([CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[CH2:20][NH:21][C:22](=[O:30])[O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27].[CH:38](N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(Cl)Cl.CCOCC.CN(C=O)C>[C:1]([CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([NH:18][C@@H:19]([CH2:31][CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)[CH2:20][N:21]([CH3:38])[C:22](=[O:30])[O:23][CH2:24][CH2:25][Si:26]([CH3:28])([CH3:29])[CH3:27])=[O:17])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11345291rel-(1R,3S)-3-Benzoylcyclohexanecarboxylic acidHCID 59382944(S)-2-(trimethylsilyl)ethyl 2-amino-3-cyclohexylpropylcarbamate

Produkt 1

HCID 671917252-(trimethylsilyl)ethyl (S)-2-(3-benzoylcyclohexanecarboxamido)-3-cyclohexylpropylmethylcarbamateAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of cis-3-benzoylcyclohexane-1-carboxylic acid (78 mg, 0.34 mmol), 2-(trimethylsilyl)ethyl (S)-2-amino-3-cyclohexylpropylcarbamate (116 mg, 0.37 mmol) and diisopropylethylamine (0.13 mL, 0.70 mmol) in CH2Cl2 (2 mL) were added solid 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 200 mg, 0.53 mmol) and DMF (0.5 mL). The mixture was stirred at rt for 3 h, diluted with ether (90 mL), washed with 5% aqueous HCl (25 mL), sat'd aqueous NaHCO3 (25 mL), and brine (25 mL) and dried over Na2SO4. Removal of the solvent under reduced pressure left an oil (260 mg) which was applied to a 2-g silica SPE cartridge and eluted sequentially with 0, 10, 25, 50, 75, and 100% EtOAc in hexanes (15 mL of each) to give six fractions. Fractions 2-4 were pooled and evaporated to afford 2-(trimethylsilyl)ethyl (S)-2-(3-benzoylcyclohexane-carboxamido)-3-cyclohexylpropylmethylcarbamate (170 mg, 91%) as an oil. MS ESI +ve m/z 528 (M+1).

Aufarbeitung

  1. washwashed with 5% aqueous HCl (25 mL)
  2. dry with materialdried over Na2SO4
  3. customRemoval of the solvent under reduced pressure
  4. waitleft an oil (260 mg) which
  5. washeluted sequentially with 0, 10, 25, 50, 75, and 100% EtOAc in hexanes (15 mL of each)
  6. customto give six fractions
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6273d671c9b540b094e82e16a227820b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455521B2

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