Triethylamine → 2-Methylpentane

HRID 471301ノート

反応式

HRID 471301 の反応式
[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

参加物

9

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2ff027de965a431c94e721d126664ed1
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

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