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Ethyl Acetate → 2-bromo-9-tert-butyl-3-methoxy-14-(1,3-thiazol-5-yl)-5,6,10,11-tetrahydro-9H-[1,4]oxazocino[7',6':4,5]pyrrolo[2,1-a]isoquinolin-8(13H)-one

HRID 1971692
ノート
印刷プレビュー

反応式

HRID 1971692 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:15](=O)[C:16]([N:18]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:19][CH2:20][O:21][CH2:22][C:23]#[C:24][C:25]3[S:29][CH:28]=[N:27][CH:26]=3)=[O:17])[CH:9]2C(O)=O)=[CH:4][C:3]=1[O:35][CH3:36].C([O-])(=O)C.[Na+].C(OCC)(=O)C.[NH4+].[OH-]>C(OC(=O)C)(=O)C.C(OCC)C>[Br:1][C:2]1[C:3]([O:35][CH3:36])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:15]4[C:16](=[O:17])[N:18]([C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:19][CH2:20][O:21][CH2:22][C:23]=4[C:24]([C:25]4[S:29][CH:28]=[N:27][CH:26]=4)=[C:9]3[C:10]=2[CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 517045Sodium AcetateHCID 669197587-Bromo-2-(2-(tert-butyl(2-(3-(thiazol-5-yl)prop-2-ynyloxy)ethyl)amino)-2-oxoacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

生成物 1

HCID 581248172-bromo-9-tert-butyl-3-methoxy-14-(1,3-thiazol-5-yl)-5,6,10,11-tetrahydro-9H-[1,4]oxazocino[7',6':4,5]pyrrolo[2,1-a]isoquinolin-8(13H)-one
収率 67.7%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 7918Acetic Anhydride溶媒

実験手順

A solution of 480 mg of 11h in 7 ml of acetic anhydride and 500 mg of anhydrous sodium acetate was heated at 105° C. for 30 min. The reaction mixture was cooled and treated with 40 ml of ice-water and stirred for 1 hr at ambient temperature to break down excess anhydride. Then, 30 ml of ethyl acetate was added and the stirred mixture was treated with cold conc. aq. NH4OH, to adjust the pH of the reaction mixture to slightly basic. The materials were extracted into ethyl acetate, washed with water, dried and concentrated. The residue was passed over a short silica column, using a gradient of toluene/ethyl acetate as eluent and the purified material thus obtained was treated with diethyl ether, to give 290 mg of 11i as white crystals; Mp 219-220° C.; Rf 0.35 (toluene/ethyl acetate 1/1). MS-ESI: [M+1] 516.04, 518.05.

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionThe materials were extracted into ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe purified material thus obtained

出典と根拠

ORDレコード
ord-08caf26be1914ab6888c999b1e57415d
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08431564B2

反応ノート

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