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Water → Benzyl 5-(tert-butyloxycarbonylamino)indole-2-carboxylate

HRID 1455898
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HRID 1455898 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([OH:20])=[O:19])=[CH:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([O:20][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:19])=[CH:12]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 158871475-(((tert-butoxy)carbonyl)amino)-1H-indole-2-carboxylic acid

생성물 1

HCID 22105409Benzyl 5-(tert-butyloxycarbonylamino)indole-2-carboxylate수율 84%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

A solution of compound 31 (2.03 g, 7.4 mmol) in DMF (50 mL) was treated with sodium bicarbonate (1.8 g, 21.4 mmol), and benzyl bromide (4 mL, 33.6 mmol). The reaction mixture was stirred for 18 h at room temperature. Water (50 mL) was added and the product was extracted with ethyl acetate (80 mL×3). The solution was dried with sodium sulfate, concentrated in vacuo to give compound 32 (2.27 g, 84% yield) as a white solid. m.p.180°-182° C. 1H NMR (DMSO-d6, ppm): 11.93 (s, 1 H, NH), 7.51-7.02 (m, 9 H, Ar--H), 5.38 (s, 2 H, CH2C6 H5), 1,48 (s, 9 H, C(CH3)3). Anal. (C21H22 N2O4 0.25H2O), C, H, N.

후처리

  1. extractionthe product was extracted with ethyl acetate (80 mL×3)
  2. dry with materialThe solution was dried with sodium sulfate
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7b5a4e2f74584964b63466994ddee434
출처 데이터셋
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05843937

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