3-tert-butoxycarbonyl-7-chloro-6-dimethylaminocarbonylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 7-Chloro-6-[1-(6-methylpyridin-2-yl)-ethylthio]-2,3,4,5-tetrahydro-1h-benzo[d]azepine hydrochloride

HRID 911473

反応式

HRID 911473 の反応式
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20]C(=O)N(C)C)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:26][C:27]1[N:32]=[C:31]([C@H:33](OS(C)(=O)=O)[CH3:34])[CH:30]=[CH:29][CH:28]=1>>[ClH:19].[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[S:20][CH:33]([C:31]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:26])[N:32]=1)[CH3:34]

参加物

3

反応物 2

HCID 576559793-tert-butoxycarbonyl-7-chloro-6-dimethylaminocarbonylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 57656393(R)-Methanesulfonic acid 1-(6-methyl-pyridin-2-yl)-ethyl ester

生成物 1

HCID 667066797-Chloro-6-[1-(6-methylpyridin-2-yl)-ethylthio]-2,3,4,5-tetrahydro-1h-benzo[d]azepine hydrochloride

実験手順

Use a method similar to the Preparation 177, except that the alkylation is conducted at 0° C., to react 3-tert-butoxycarbonyl-7-chloro-6-dimethylcarbamoylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine with (R)-methanesulfonic acid 1-(6-methyl-pyridin-2-yl)-ethyl ester. Use a method similar to the General Procedure 1-5, basic workup, and a method similar to the General Procedure 2-2 to give the title compound as a white solid. MS (APCI+) m/z: 333 (M+H)+; ee >97%, tR=6.53 min. (Chiral HPLC: Chiralpak OJ 120 Å 4.6×250 mm, 45° C.; eluent: 20% isopropanol with 0.05% triethylamine in SFC, flow rate 2 mL/min, LTV detector at 234 nm).

後処理

  1. customsimilar to the Preparation 177
  2. customis conducted at 0° C.

出典と根拠

ORDレコード
ord-dcdc14d25c794141893369e83fcca90d
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

関連ノート

読み込み中…