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Triphenylphosphine → (R)-methyl 2-(tert-butoxycarbonylamino)-2-(2-oxoethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate

HRID 579480
ノート
印刷プレビュー

反応式

HRID 579480 の反応式
[CH2:1]([C@:4]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([CH2:9][CH2:10][CH2:11][CH2:12][B:13]1[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]1)[C:5]([O:7][CH3:8])=[O:6])[CH:2]=C.[O:30]=[O+][O-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:26]([O:25][C:23]([NH:22][C@@:4]([CH2:1][CH:2]=[O:30])([CH2:9][CH2:10][CH2:11][CH2:12][B:13]1[O:14][C:15]([CH3:20])([CH3:21])[C:16]([CH3:18])([CH3:19])[O:17]1)[C:5]([O:7][CH3:8])=[O:6])=[O:24])([CH3:29])([CH3:28])[CH3:27]
参加物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 11776TriphenylphosphineHCID 24823Ozone2 回HCID 66833177(R)-methyl 2-allyl-2-(tert-butoxycarbonylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate

生成物 1

HCID 71600280(R)-methyl 2-(tert-butoxycarbonylamino)-2-(2-oxoethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate収率 67%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

A solution of (R)-methyl 2-allyl-2-(tert-butoxycarbonylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (1.90 g, 4.62 mmol) in dichloromethane (90 mL, 0.05 M) was cooled to −78° C. and treated with ozone until a pale blue-gray color appeared. After TLC indicated the absence of starting material, the ozone inlet tube was replaced with nitrogen and nitrogen was bubbled through the solution for 20 min to remove any excess ozone. Triphenylphosphine (3.6 g, 13.8 mmol, 3 equiv) was added in one portion, the cooling bath was removed and the mixture was stirred for 4 h. The solution was concentrated and purified by MPLC (1-50% ethyl acetate in heptane over 6 CV) and gave (R)-methyl 2-(tert-butoxycarbonylamino)-2-(2-oxoethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate as a colorless oil (1.28 g, 67%). Rf 0.55 (30% ethyl acetate in heptane); 1H NMR (CDCl3, 300 MHz) δ 9.66 (s, 1H), 5.62 (br s, 1H), 3.75 (s, 3H), 3.60 (br d, J=17.4 Hz, 1H), 2.95 (d, J=17.4 Hz, 1H), 2.30-2.15 (m, 1H), 1.70-1.54 (m, 1H), 1.40 (s, 9H), 1.39-1.24 (m, 4H), 0.74 (t, J=7.8 Hz, 2H); ESI-LCMS m/z calcd for C20H36BNO7: expected 413.3. found 414.3 (M+H)+.

後処理

  1. customwas bubbled through the solution for 20 min
  2. customto remove any excess ozone
  3. customthe cooling bath was removed
  4. concentrationThe solution was concentrated
  5. custompurified by MPLC (1-50% ethyl acetate in heptane over 6 CV)

出典と根拠

ORDレコード
ord-3e44a1eef9a746d282a27c6d095adbf3
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040703B2

反応ノート

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