(S)-4-(2-(2-carboxyacetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide → (S)-4-(2-(3-(4-(N-(tert-butoxycarbonyl)-methylsulfonamido)-3-(cyclopropylmethoxy)benzyloxy)-3-oxopropanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide

HRID 1776489ノート

反応式

HRID 1776489 の反応式
[C:1]([CH2:4][C:5]([O:7][C@H:8]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH:26]([F:28])[F:27])=[C:21]([O:29][CH2:30][CH:31]2[CH2:33][CH2:32]2)[CH:20]=1)[CH2:9][C:10]1[C:15]([Cl:16])=[CH:14][N+:13]([O-:17])=[CH:12][C:11]=1[Cl:18])=[O:6])([OH:3])=[O:2].[CH:34]1([CH2:37][O:38][C:39]2[CH:44]=[C:43]([CH2:45]O)[CH:42]=[CH:41][C:40]=2[N:47]([S:55]([CH3:58])(=[O:57])=[O:56])[C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51])[CH2:36][CH2:35]1>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:50]([O:49][C:48]([N:47]([C:40]1[CH:41]=[CH:42][C:43]([CH2:45][O:2][C:1](=[O:3])[CH2:4][C:5]([O:7][C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH:26]([F:28])[F:27])=[C:21]([O:29][CH2:30][CH:31]3[CH2:32][CH2:33]3)[CH:20]=2)[CH2:9][C:10]2[C:15]([Cl:16])=[CH:14][N+:13]([O-:17])=[CH:12][C:11]=2[Cl:18])=[O:6])=[CH:44][C:39]=1[O:38][CH2:37][CH:34]1[CH2:35][CH2:36]1)[S:55]([CH3:58])(=[O:56])=[O:57])=[O:54])([CH3:53])([CH3:51])[CH3:52]

参加物

5

反応物 2

HCID 86679438(S)-4-(2-(2-carboxyacetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxideHCID 86679440Tert-butyl 2-(cyclopropylmethoxy)-4-(hydroxymethyl)phenyl(methylsulfonyl)carbamate

生成物 1

HCID 86679439(S)-4-(2-(3-(4-(N-(tert-butoxycarbonyl)-methylsulfonamido)-3-(cyclopropylmethoxy)benzyloxy)-3-oxopropanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of (S)-4-(2-(2-carboxyacetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (50 mg, 0.099 mmol), tert-butyl 2-(cyclopropylmethoxy)-4-(hydroxymethyl)phenyl-(methylsulfonyl)-carbamate (73 mg, 0.2 mmol), DMAP (14.5 mg, 0.12 mmol), and ECD (57 mg, 0.3 mmol) in DMF (1.5 ml) was stirred at RT overnight. The reaction mixture was quenched with water, and the product was extracted with EtOAc. The organic phase was washed with HCl 1M, NaHCO3 sat. sol. and brine. The organic layer was dried over Na2SO4 and evaporated to dryness. The crude (70 mg) was used for the next step without any further purification.

後処理

  1. customThe reaction mixture was quenched with water
  2. extractionthe product was extracted with EtOAc
  3. washThe organic phase was washed with HCl 1M, NaHCO3 sat. sol. and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude (70 mg) was used for the next step without any further purification

出典と根拠

ORDレコード
ord-7f998f934b294e5795b6498f3ad3768f
出典データセット
uspto-grants-2016_02
特許番号
US09265768B2

反応ノート

読み込み中…