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Triethylamine → 2-[2-(3,5-Difluoro-benzylcarbamoyl)-propionylamino]-3-(1H-indol-3-yl)-propionic acid tert-butyl ester

HRID 2223249
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HRID 2223249 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([F:17])[CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[CH:8]([CH3:12])[C:9]([OH:11])=O.Cl.[C:19]([O:23][C:24](=[O:37])[C@H:25]([CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)[NH2:26])([CH3:22])([CH3:21])[CH3:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[C:19]([O:23][C:24](=[O:37])[CH:25]([NH:26][C:9](=[O:11])[CH:8]([C:7](=[O:13])[NH:6][CH2:5][C:4]1[CH:14]=[C:15]([F:17])[CH:16]=[C:2]([F:1])[CH:3]=1)[CH3:12])[CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)([CH3:22])([CH3:20])[CH3:21]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11514895(S)-tert-butyl 2-amino-3-(1H-indol-3-yl)propanoate hydrochlorideHCID 21091473N-(3,5-difluoro-benzyl)-2-methyl-malonamic acid

생성물 1

HCID 692836102-[2-(3,5-Difluoro-benzylcarbamoyl)-propionylamino]-3-(1H-indol-3-yl)-propionic acid tert-butyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

N-(3,5-Difluoro-benzyl)-2-methyl-malonamic acid (3.00 g, 12.3 mmol), L-tryptophan-tert-butylester hydrochloride (3.66 g, 12.3 mmol), TBTU (O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium-tetrafluoroborate, 3.96 g, 12.3 mmol) and triethylamin (3.74 g, 3.70 mmol) were dissolved in DMF (15 ml) and stirred for 5 h at r.t. The reaction mixture was poured into water and the product mixture was extracted with ethyl acetate. The organic layers were dried (Na2SO4). After evaporation of the solvent, the title compound, MS: m/e=486.4 (M+H+), (6.45 g, quant.) was obtained by chromatographic purification of the residue (silica gel, MeOH, CH2Cl2).

후처리

  1. extractionthe product mixture was extracted with ethyl acetate
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. customAfter evaporation of the solvent

출처 및 근거

ORD 기록
ord-f9af4bff7cd243e6b0e6963277ceaea3
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07375099B2

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