ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Sodium Hydroxide → (R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid

HRID 1526418
ノート
印刷プレビュー

反応式

HRID 1526418 の反応式
[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[N:4]2[CH2:27][CH2:28][C@H:29]([CH2:30][C:31]([O:33]CC)=[O:32])[C:3]=12.[OH-].[Na+]>O1CCOCC1.CO>[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([C:23]([F:24])([F:25])[F:26])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[N:4]2[CH2:27][CH2:28][C@H:29]([CH2:30][C:31]([OH:33])=[O:32])[C:3]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 68240766(R)-ethyl 2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

生成物 1

HCID 53362086(R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid収率 94.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 31275
1,4-Dioxane
溶媒

実験手順

To a solution of (R)-ethyl 2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (54.6 g, 107 mmol) in dioxane (750 mL) and MeOH (75 mL) was added NaOH (aq. 3N, 89.0 mL, 268 mmol). The mixture was stirred at room temperature for 17 h, concentrated in vacuo to approx 150 mL, and acidified with aqueous 3N HCl (300 mL). The resulting slurry was shaken and the solid filtered, washed with H2O (twice), hexanes and dried in a vacuum oven (50° C., 2 Torr, 15 h) to give (R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid (51.3 g, 101 mmol, 94% yield, >98% ee) as a white solid. Exact mass calculated for C24H23ClF3NO4: 481.1, found: LCMS m/z=482.2, [M+H+]; 1H NMR (400 MHz, CD3CN) δ ppm 1.33 (d, J=6.0 Hz, 6 H), 2.34 (m, 1 H), 2.58 (dd, J1=16.5, J2=9.7 Hz, 1 H), 2.86 (m, 1 H), 3.06 (dd, J1=16.5, J2=4.2 Hz, 1 H), 3.73 (m, 1 H), 4.01 (m, 1 H), 4.14 (ddd, J1=9.9, J2=8.5 Hz, J3=4.9 Hz 1 H), 4.75 (sep, J=6.0 Hz, 1 H), 5.08 (s, 2 H), 6.87 (dd, J1=8.8, J2=2.4 Hz, 1 H), 7.01 (d, J=2.4 Hz, 1 H), 7.18 (d, J=8.6 Hz, 1 H), 7.21 (d, J=8.8 Hz, 1 H), 7.63 (dd, J1=8.6, J2=2.1 Hz, 1 H), 7.68 (d, J=2.1 Hz, 1 H), 9.10 (bs, 1 H).

後処理

  1. concentrationconcentrated in vacuo to approx 150 mL
  2. stirringThe resulting slurry was shaken
  3. filtrationthe solid filtered
  4. washwashed with H2O (twice), hexanes
  5. customdried in a vacuum oven (50° C., 2 Torr, 15 h)

出典と根拠

ORDレコード
ord-526ea5fd9b8d4de791b3c2deff4b40e8
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085581B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート