Triethylamine → 2-Methylpentane

HRID 1689529Notes

Reaction equation

HRID 1689529 reaction equation
[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

Participants

9

Reactant 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

Product 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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ff960d8b0b0e4146aa347e233117e3a3
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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