N-(Diphenylmethylene)glycine tert-butyl ester → 4-[3-[(Benzhydrylidene-amino)-tert-butoxycarbonyl-methyl]-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-butyryl]-2-methyl-benzoic acid tert-butyl ester

HRID 589643

反応式

HRID 589643 の反応式
[C:1]([O:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:28])/[CH:14]=[C:15](\[C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)/[C:16]([F:19])([F:18])[F:17])=[CH:9][C:8]=1[CH3:29])([CH3:4])([CH3:3])[CH3:2].[C:31]([O:35][C:36](=[O:52])[CH2:37][N:38]=[C:39]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([CH3:34])([CH3:33])[CH3:32].O.[OH-].[Cs+].C=CCO[C@H](C1C2C(=CC=CC=2)N=CC=1)[C@H]1[N+]2(CC3C4C(=CC=CC=4)C=C4C=3C=CC=C4)C[C@H](C=C)[C@@H](CC2)C1.[Br-]>ClCCl.O>[C:1]([O:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:28])[CH2:14][C:15]([CH:37]([N:38]=[C:39]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:52])([C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)[C:16]([F:17])([F:19])[F:18])=[CH:9][C:8]=1[CH3:29])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 688171N-(Diphenylmethylene)glycine tert-butyl esterHCID 10886583O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromideHCID 23679066Caesium hydroxide--water (1/1/1)HCID 866959924-[(E)-3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-2-methyl-benzoic acid tert-butyl ester

生成物 1

HCID 866960024-[3-[(Benzhydrylidene-amino)-tert-butoxycarbonyl-methyl]-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-butyryl]-2-methyl-benzoic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Similarly, 4-[(E)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-2-methyl-benzoic acid tert-butyl ester (1 gl) and (benzhydrylidene-amino)-acetic acid tert-butyl ester (322 mg) were dissolved in dichloromethane (13 ml). Cesium hydroxide hydrate (1.82 g) and O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (66 mg) were added and the resulting mixture was stirred at −75 C for 18 hours. At this time water was added and the reaction mixture was extracted with ethyl acetate. The organic layers were combined, dried over magnesium sulfate, filtered and evaporated in vacuo to give a crude residue which was purified by flash chromatography (0% to 05% dichloromethane in heptane) to afford 4-[3-[(Benzhydrylidene-amino)-tert-butoxycarbonyl-methyl]-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-butyryl]-2-methyl-benzoic acid tert-butyl ester (426 mg) as a yellow foam and a single diastereoisomer. 19F NMR (376 MHz, CDCl3) δ −61 ppm (1 diastereoisomer).

後処理

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto give a crude residue which
  6. customwas purified by flash chromatography (0% to 05% dichloromethane in heptane)

出典と根拠

ORDレコード
ord-d0979ada8d40478089b46c77d2510ebe
出典データセット
uspto-grants-2016_01
特許番号
US09233920B2

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