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Hydrochloric Acid → ({[(14-Cyclohexyl-3-methoxy-6-methyl-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocin-11-yl)carbonyl]amino}sulfonyl)acetic acid

HRID 1714000
ノート
印刷プレビュー

反応式

HRID 1714000 の反応式
C[O:2][C:3](=[O:39])[CH2:4][S:5]([NH:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]2[C:15]([CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[C:16]3[C:23]4[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:22]=4[CH2:21][N:20]([CH3:30])[CH2:19][CH2:18][N:17]3[C:31]=2[CH:32]=1)=[O:10])(=[O:7])=[O:6].O.[OH-].[Na+].Cl>O1CCOCC1>[CH:33]1([C:15]2[C:14]3[CH:13]=[CH:12][C:11]([C:9]([NH:8][S:5]([CH2:4][C:3]([OH:39])=[O:2])(=[O:7])=[O:6])=[O:10])=[CH:32][C:31]=3[N:17]3[CH2:18][CH2:19][N:20]([CH3:30])[CH2:21][C:22]4[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=4[C:16]=23)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 11613717HCID 11613717、化合物

生成物 1

HCID 42640441({[(14-Cyclohexyl-3-methoxy-6-methyl-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocin-11-yl)carbonyl]amino}sulfonyl)acetic acid収率 72%

試薬・触媒・溶媒 1

HCID 31275
1,4-Dioxane
溶媒

実験手順

To a solution of methyl({[(14-cyclohexyl-3-methoxy-6-methyl-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocin-11-yl)carbonyl]amino}sulfonyl)acetate (from example 5) in dioxane (0.04 M) was added an equal volume of water and 4 eq of NaOH (1 N aqueous solution). The reaction was stirred vigorously at RT for 1 h. The reaction was acidified with aqueous HCl (1 N) and reduced in vacuo to remove dioxane. The resultant aqueous slurry was diluted with MeCN and water and freeze dried to leave a white powder. The crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×100 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound as a white powder (72%).

後処理

  1. customto remove dioxane
  2. additionThe resultant aqueous slurry was diluted with MeCN and water and freeze
  3. customdried
  4. customto leave a white powder
  5. customThe crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×100 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
  6. additionFractions containing the pure compound
  7. customfreeze dried

出典と根拠

ORDレコード
ord-5c9dd2bed41b4fffabfe682f6d29ca11
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07795247B2

反応ノート

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