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5-Bromo-2-chlorobenzoic acid → 4-[(2-Chloro-5-bromophenylcarbonyl)amino]-N-[(1,1-dimethylethyoxy)carbonyl]-L-phenylalanine Methyl Ester

HRID 393470
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HRID 393470 반응식
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[Cl:22][C:23]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:24]=1[C:25](O)=[O:26].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:25]([C:24]2[CH:28]=[C:29]([Br:32])[CH:30]=[CH:31][C:23]=2[Cl:22])=[O:26])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 331275-Bromo-2-chlorobenzoic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 110118554-Amino-N-((1,1-dimethylethoxy)carbonyl)-L-phenylalanine methyl ester

생성물 1

HCID 536551064-[(2-Chloro-5-bromophenylcarbonyl)amino]-N-[(1,1-dimethylethyoxy)carbonyl]-L-phenylalanine Methyl Ester
수율 10%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 4-amino-N-[(1,1-dimethylethoxy)carbonyl)-L-phenylalanine methyl ester (20 mmol, 5.88 g), 2-chloro-5-bromobenzoic acid (22 mmol, 5.18 g) and HBTU (22 mmol, 8.34 g) in DMF (70 mL) was added diisopropylethylamine (50 mmol, 8.7 mL) at room temperature. The suspension was stirred for 48 h at which time TLC analysis of the mixture indicated the absence of starting material. Then, the mixture was diluted with water (100 mL) and the solids were collected by filtration and washed with water (150 mL). After air drying, the crude product was purified by silica gel column chromatography to obtain 1.02 g (10%) of a white solid: mp 158-161° C. HR MS (C22H24BrClN2O5): Ob, 533.0442. Calcd mass, 533.0455 (M+Na).

후처리

  1. filtrationthe solids were collected by filtration
  2. washwashed with water (150 mL)
  3. customAfter air drying
  4. customthe crude product was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f2ab16811f8c405395b187825311237c
출처 데이터셋
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06806365B2

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