2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → tert-butyl 2-(N-(3-bromo-5-fluorobenzyl)-2,2-dimethylchroman-6-sulfonamido)acetate

HRID 1805954ノート

反応式

HRID 1805954 の反応式
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12]([NH:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])(=[O:14])=[O:13])[CH:8]=2)[O:3]1.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[Br:43][C:44]1[CH:49]=[C:48]([F:50])[CH:47]=[C:46]([CH2:51]Br)[CH:45]=1>CC#N>[Br:43][C:44]1[CH:45]=[C:46]([CH:47]=[C:48]([F:50])[CH:49]=1)[CH2:51][N:15]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[S:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]([CH3:24])([CH3:1])[CH2:11][CH2:10]2)(=[O:14])=[O:13]

参加物

5

反応物 3

HCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 235096191-Bromo-3-(bromomethyl)-5-fluorobenzeneHCID 58409094Tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate

生成物 1

HCID 58409093tert-butyl 2-(N-(3-bromo-5-fluorobenzyl)-2,2-dimethylchroman-6-sulfonamido)acetate収率 90.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

To the solution of tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate (500 mg, 1.407 mmol) in MeCN (15 mL) was added resin-supported BEMP (786 mg, 1.547 mmol) and 1-bromo-3-(bromomethyl)-5-fluorobenzene (501 mg, 1.871 mmol). The mixture was heated in a microwave synthesizer at 90° C. for 3 hours. The reaction mixture was filtered, rinsed alternatively by dichloromethane and methanol. The filtrate was concentrated to give a reddish orange residue, which was purified by silica chromatography to obtain a white powder (688 mg, 86% yield). 1H NMR (500 MHz, CDCl3) δ 7.56 (d, J=6.2 Hz, 2H), 7.18-7.12 (m, 2H), 6.95 (d, J=9.0 Hz, 1H), 6.87-6.80 (m, 1H), 4.46 (s, 2H), 3.82 (s, 2H), 2.80 (t, J=6.7 Hz, 2H), 1.83 (t, J=6.7 Hz, 2H), 1.36 (s, 9H), 1.35 (s, 6H). 19F NMR (471 MHz, CDCl3) δ LRMS [ESI, MH+] m/z calcd for C24H30BrFNO5S 542.10, found 542.1.

後処理

  1. filtrationThe reaction mixture was filtered
  2. washrinsed alternatively by dichloromethane and methanol
  3. concentrationThe filtrate was concentrated
  4. customto give a reddish orange residue, which
  5. customwas purified by silica chromatography

出典と根拠

ORDレコード
ord-bfc241ff11a442879fb30c477b0e43b8
出典データセット
uspto-grants-2013_01
特許番号
US08354548B2

反応ノート

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