Triethylamine → 2-Methylpentane

HRID 471301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471301
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([N:9]2[CH2:14][C:13]3([CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:22]=[C:23]([CH:32]=[CH:33][CH:34]=4)[CH2:24][CH2:25][O:26][CH2:27][CH2:28][C:29](O)=[O:30])[CH2:16][CH2:15]3)[O:12][CH2:11][CH2:10]2)=[O:8])[N:6]=1.[CH3:35][O:36][CH:37]([O:46][CH3:47])[CH2:38][NH:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1.C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C.C(OCC)(=O)C.O>[CH3:24][CH2:23][CH2:22][CH:21]([CH3:34])[CH3:20].[CH:40]1([N:39]([CH2:38][CH:37]([O:46][CH3:47])[O:36][CH3:35])[C:29](=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24][C:23]2[CH:32]=[CH:33][CH:34]=[C:21]([CH2:20][N:17]3[CH2:18][CH2:19][C:13]4([O:12][CH2:11][CH2:10][N:9]([C:7]([C:5]5[N:6]=[C:2]([CH3:1])[S:3][CH:4]=5)=[O:8])[CH2:14]4)[CH2:15][CH2:16]3)[CH:22]=2)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 3024915N-(2,2-dimethoxyethyl)cyclohexanamineHCID 579890083-(3-((4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoic acid

Produkt 2

HCID 78922-MethylpentaneHCID 57989141N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-((4-(2-methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-(3-((4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoic acid (Example 277, step b) was dissolved in DMF (10 mL), and N-(2,2-dimethoxyethyl)cyclohexanamine (WO2008075025) (0.93 g), triethylamine (2.88 mL) and T3P (3.95 mL) were added. The reaction was stirred overnight and partioned between water (100 mL) and ethyl acetate (100 mL). The layers were separated and the aqueous extracted with ethyl acetate (2×100 mL). The combined organics were washed with saturated sodium bicarbonate solution (100 mL), brine (100 mL), dried over sodium sulphate, filtered and evaporated. The residue was purified by flash silica column chromatography eluting with 47.5:47.5:5 ethyl acetate:i-hexane:triethylamine to 95:5 ethyl acetate:triethylamine gradient to afford the subtitled compound as a colorless oil. Yield 0.9 g.

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous extracted with ethyl acetate (2×100 mL)
  3. washThe combined organics were washed with saturated sodium bicarbonate solution (100 mL), brine (100 mL)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash silica column chromatography
  8. washeluting with 47.5:47.5:5 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2ff027de965a431c94e721d126664ed1
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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