Pivaloyl chloride → HCID 86700014、化合物

HRID 530569

反応式

HRID 530569 の反応式
[Li]CCCC.[CH2:6]([N:13]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:27][C:28]([CH3:33])([CH3:32])[C:29](Cl)=[O:30]>C1COCC1>[CH2:20]([N:13]([CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C@@H:14]([C:29](=[O:30])[C:28]([CH3:33])([CH3:32])[CH3:27])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

5

反応物 3

HCID 62493Pivaloyl chlorideHCID 3553452Ethyl 2-(dibenzylamino)acetateHCID 178418339Butyllithium

生成物 1

HCID 86700014HCID 86700014、化合物収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In a round bottomed flask, at −78° C., under argon atmosphere, a solution of DIPA (0.29 mL, 2.12 mmol) in dry THF (10 ml) was treated with n-BuLi (2.5 M in n-hexane, 0.776 mL, 1.94 mmol). After 30 min a solution of ethyl 2-(dibenzylamino)-acetate [prepared as described in Example 47, step 1] (0.5 g, 1.77 mmol) in dry THF (10 mL) was added dropwise via cannula. After 15 min, trimethylacetyl chloride (0.53 mL, 3.53 mmol) was added dropwise at −78° C. and the mixture stirred for 10 min at rt. The reaction was then quenched with H2O, and Et2O was subsequently added. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give a crude product as an oil. Purification by column chromatography using a Teledyne ISCO apparatus, eluting with Cy:AcOEt (98:2) gave the title compound (0.492 g, 76%) as a colorless oil. MS (ESI) m/z: 368 [M−H]+; (ESI) m/z: 366 [M−H]−. 1H NMR (DMSO-d6) δ 0.93 (s, 9H), 1.16-1.25 (m, 3H), 3.79 (d, J=13.97 Hz, 2H), 3.98 (d, J=13.96 Hz, 2H), 4.07-4.25 (m, 2H), 4.60 (s, 1H), 7.20-7.41 (m, 10H).

後処理

  1. customThe reaction was then quenched with H2O, and Et2O
  2. additionwas subsequently added
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude product as an oil
  8. customPurification by column chromatography
  9. washeluting with Cy

出典と根拠

ORDレコード
ord-9cac8299a5594b31aefd21dd224bf4f0
出典データセット
uspto-grants-2016_05
特許番号
US09353075B2

関連ノート

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