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Dimethyl methylphosphonate → (7-tert-Butoxycarbonylamino-2-oxo-heptyl)-phosphonic acid dimethyl ester

HRID 860092
ノート
印刷プレビュー

反応式

HRID 860092 の反応式
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])CCC.O=C1CCC(=O)N1[O:20][C:21](=O)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>C1COCC1>[CH3:4][O:3][P:2]([CH2:1][C:21](=[O:20])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])(=[O:7])[O:5][CH3:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 12958Dimethyl methylphosphonateHCID 5074016Boc-6-Ahx-OSuHCID 178418339Butyllithium

生成物 1

HCID 20622500(7-tert-Butoxycarbonylamino-2-oxo-heptyl)-phosphonic acid dimethyl ester収率 105.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

A solution of dimethyl methylphosphonate (9.308 g, 75.01 mmol) in THF (30 mL) was cooled to −78 ° C. and treated with n-butyllithium (29.5 mL of 2.5 M). The reaction mixture was stirred at −78 ° C. for 10 min, followed by addition of 6-tert-butoxycarbonylamino-hexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (24-1) (5.060 g, 15.41 mmol) in THF (30 mL). After 15 min the reaction was quenched with aqueous NH4Cl and allowed to warm to room temperature overnight. The water was extracted three times with ethyl acetate and the combined organics washed with brine and dried (Na2SO4). The solvent was removed in vacuo to afford the title compound 24-2 as a pale yellow oil (5.5 g).

後処理

  1. customAfter 15 min the reaction was quenched with aqueous NH4Cl
  2. temperatureto warm to room temperature overnight
  3. extractionThe water was extracted three times with ethyl acetate
  4. washthe combined organics washed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-632d255c771449be809672fa3420dff6
出典データセット
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07153862B2

反応ノート

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