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

HRID 860092
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HRID 860092 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-632d255c771449be809672fa3420dff6
출처 데이터셋
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07153862B2

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