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Toluene → 4-(2-Methyl-thiazol-4-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

HRID 1929199
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HRID 1929199 반응식
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][OH:8])[N:6]=1.[CH3:9][CH2:10][O:11][C:12]([C:14]1[N:15]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:16]2[C:21]([CH:22]=1)=[C:20](OCC1C=CC=CC=1)[CH:19]=[CH:18][CH:17]=2)=[O:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>C1COCC1>[CH3:9][CH2:10][O:11][C:12]([C:14]1[N:15]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[C:16]2[C:21]([CH:22]=1)=[C:20]([O:8][CH2:7][C:5]1[N:6]=[C:2]([CH3:1])[S:3][CH:4]=1)[CH:19]=[CH:18][CH:17]=2)=[O:13]
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참가 물질

6

반응물 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 10582809(2-Methyl-1,3-thiazol-4-yl)methanolHCID 591526751-tert-butyl 2-ethyl 4-(benzyloxy)-1H-indole-1,2-dicarboxylate

생성물 1

HCID 668421144-(2-Methyl-thiazol-4-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
0 °C

실험 절차

(2-Methyl-thiazol-4-yl)-methanol (168, 670 mg, 5.2 mmol) is dissolved in 12 ml of dry THF under argon, followed by addition of 4-Hydroxy-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (102, see example 42, 1.58 g, 5.2 mmol), triphenylphosphine (1.63 g, 6.2 mmol).) and the solution is cooled to 0° C. A 40% solution of ethyl azadicarboxylate in toluene (2.7 ml, 6.2 mmol) is added dropwise and the mixture is stirred for 2.5 h at 0° C. The solvents are removed under reduced pressure and the residue is dissolved in ethyl acetate and washed with sodium hydrogencarbonate solution and brine. The organic layers are dried over sodium sulphate, filtrated and evaporated. The crude product is purified by flash chromatography (silica gel, ethyl acetate/hexanes 3:7)

후처리

  1. customThe solvents are removed under reduced pressure
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with sodium hydrogencarbonate solution and brine
  4. dry with materialThe organic layers are dried over sodium sulphate
  5. filtrationfiltrated
  6. customevaporated
  7. customThe crude product is purified by flash chromatography (silica gel, ethyl acetate/hexanes 3:7)

출처 및 근거

ORD 기록
ord-0c8a4103f6754916a1d8b8c0e42a152b
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183366B2

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