Triethylamine → HCID 23627686、化合物

HRID 1171906ノート

反応式

HRID 1171906 の反応式
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37].C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[CH2:39]([O:38][C:36]([N:13]1[CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9][C@@H:8]1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:37])[CH3:40]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine

生成物 1

HCID 23627686HCID 23627686、化合物収率 34.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2) (73 mg, 0.2 mmol) in THF (0.5 mL) at room temperature was treated with triethylamine (28 μL, 0.2 mmol) followed by ethyl chloroformate (19 μL, 0.2 mmol). The reaction mixture was stirred for 2 h then diluted with EtOAc (2 mL) followed by a saturated aqueous NaHCO3 solution (1 mL). The organic phase was isolated and further washed with an additional portion of a saturated aqueous NaHCO3 solution (1 mL) followed by a brine solution (1 mL). The organic component was dried over MgSO4, filtered, and evaporated to an oil which was purified by silica gel flash chromatography with 10% then 30% EtOAc/hexane as eluant to afford product as an oil (30 mg, 34%). 1H NMR (CDCl3) 1.25 (t, J=7.2, 3H), 1.60-1.65 (m, 2H), 1.79-1.89 (m, 3H), 1.92-2.00 (m, 2H), 2.60-2.72 (m, 2H), 2.95 (dd, J=12.9, 4.8, 1H), 3.20-3.28 (m, 2H), 3.33-3.42 (m, 2H), 3.79 (s, 3H), 4.08-4.13 (m, 3H), 4.40 (br s, 1H), 4.69-4.72 (m, 1H), 6.39 (dd, J=8.6, 2.4, 1H), 6.47 (s, 1H), 6.77 (d, J=8.6, 1H), 7.22-7.34 (m, 5H). LC/MS 7.81 min, [M+1]+ 439.

後処理

  1. customThe organic phase was isolated
  2. washfurther washed with an additional portion of a saturated aqueous NaHCO3 solution (1 mL)
  3. dry with materialThe organic component was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to an oil which
  6. customwas purified by silica gel flash chromatography with 10%

出典と根拠

ORDレコード
ord-b1b813806dc44a0586fbf174ff39c0cb
出典データセット
uspto-grants-2010_11
特許番号
US07829713B2

反応ノート

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