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Diisopropylethylamine → methyl (2S,3R)-3-(difluoromethoxy)-1-oxo-1-((S)-2-(5-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate

HRID 1751358
ノート
印刷プレビュー

反応式

HRID 1751358 の反応式
[F:1][CH:2]([F:15])[O:3][C@H:4]([CH3:14])[C@H:5]([NH:9][C:10]([O:12][CH3:13])=[O:11])[C:6]([OH:8])=O.[NH:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]1[NH:22][C:23]([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[C:31]([B:36]4[O:40][C:39]([CH3:42])([CH3:41])[C:38]([CH3:44])([CH3:43])[O:37]4)[CH:32]=3)[CH:27]=2)=[CH:24][N:25]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[F:15][CH:2]([F:1])[O:3][C@H:4]([CH3:14])[C@H:5]([NH:9][C:10](=[O:11])[O:12][CH3:13])[C:6](=[O:8])[N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]1[NH:22][C:23]([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[C:31]([B:36]4[O:40][C:39]([CH3:42])([CH3:41])[C:38]([CH3:44])([CH3:43])[O:37]4)[CH:32]=3)[CH:27]=2)=[CH:24][N:25]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69675543HCID 69675543、化合物HCID 86702706HCID 86702706、化合物

生成物 1

HCID 67681934
methyl (2S,3R)-3-(difluoromethoxy)-1-oxo-1-((S)-2-(5-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate
収率 48%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (2S,3R)-3-(difluoromethoxy)-2-(methoxycarbonylamino)butanoic acid (205 mg, 0.9 mmol) and (S)-2-(pyrrolidin-2-yl)-5-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1H-imidazole (315 mg, 0.8 mmol) in dimethylformamide (8 mL) was added HATU (325 mg, 0.85 mmol) and diisopropylethylamine (0.565 mL, 3.2 mmol). The reaction was stirred for 1 hour and then diluted with ethyl acetate. The organic layer was washed twice with saturated NaHCO3 solution and brine, dried (MgSO4) and concentrated. The resulting residue was purified by flash chromatography to yield methyl (2S,3R)-3-(difluoromethoxy)-1-oxo-1-((S)-2-(5-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate (230 mg, 47%). LCMS-ESI+: calculated for C30H37BF2N4O6: 598.45; observed [M+1]+: 599.31.

後処理

  1. washThe organic layer was washed twice with saturated NaHCO3 solution and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe resulting residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-e87066876c734d49b8361ae140f6bbad
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09156823B2

反応ノート

読み込み中…

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