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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
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HRID 1971692 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 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
수율 67.7%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 7918Acetic Anhydride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-08caf26be1914ab6888c999b1e57415d
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431564B2

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