Hydrochloric Acid → (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3-(3-(cyclopropylmethoxy)-4-(methylsulfonamido)-benzyloxy)-3-oxopropanoyloxy)ethyl)pyridine 1-oxide

HRID 1776490ノート

反応式

HRID 1776490 の反応式
C(OC([N:8]([C:13]1[CH:52]=[CH:51][C:16]([CH2:17][O:18][C:19](=[O:50])[CH2:20][C:21]([O:23][C@H:24]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH:42]([F:44])[F:43])=[C:37]([O:45][CH2:46][CH:47]3[CH2:49][CH2:48]3)[CH:36]=2)[CH2:25][C:26]2[C:31]([Cl:32])=[CH:30][N+:29]([O-:33])=[CH:28][C:27]=2[Cl:34])=[O:22])=[CH:15][C:14]=1[O:53][CH2:54][CH:55]1[CH2:57][CH2:56]1)[S:9]([CH3:12])(=[O:11])=[O:10])=O)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[Cl:34][C:27]1[CH:28]=[N+:29]([O-:33])[CH:30]=[C:31]([Cl:32])[C:26]=1[CH2:25][C@@H:24]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH:42]([F:43])[F:44])=[C:37]([O:45][CH2:46][CH:47]2[CH2:48][CH2:49]2)[CH:36]=1)[O:23][C:21](=[O:22])[CH2:20][C:19]([O:18][CH2:17][C:16]1[CH:51]=[CH:52][C:13]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:14]([O:53][CH2:54][CH:55]2[CH2:57][CH2:56]2)[CH:15]=1)=[O:50]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 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

生成物 1

HCID 71542917(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3-(3-(cyclopropylmethoxy)-4-(methylsulfonamido)-benzyloxy)-3-oxopropanoyloxy)ethyl)pyridine 1-oxide収率 16.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

(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 (70 mg, 0.08 mmol) was dissolved in DCM (1 ml), and HCl 4M in Dioxane (500 μM) was added. The mixture was stirred at RT for 3 hours. The reaction was quenched with water, and the product was extracted with EtOAc. The organic phase was dried over Na2SO4 and evaporated to dryness. The crude was purified by Preparative reverse-phase HPLC to yield 10 mg of the final product (Yield: 16%).

後処理

  1. customThe reaction was quenched with water
  2. extractionthe product was extracted with EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated to dryness
  5. customThe crude was purified by Preparative reverse-phase HPLC

出典と根拠

ORDレコード
ord-e18bb6828c2b478a9fbf82b449777177
出典データセット
uspto-grants-2016_02
特許番号
US09265768B2

反応ノート

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