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Triethylamine → (3R*,4R*)-3-({Cyclopropyl-[2-(3-nitro-phenyl)-acetyl]-amino}-methyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1158361
ノート
印刷プレビュー

反応式

HRID 1158361 の反応式
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N+:25]([C:28]1[CH:29]=[C:30]([CH2:34][C:35]([OH:37])=O)[CH:31]=[CH:32][CH:33]=1)([O-:27])=[O:26].[C:38]([O:42][C:43]([N:45]1[CH2:49][C@@H:48]([CH2:50][N:51]([CH:68]([CH3:70])[CH3:69])[C:52](=[O:67])[C:53]2[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[C:55]([O:61][CH2:62][CH2:63][CH2:64][O:65][CH3:66])[CH:54]=2)[C@H:47]([CH2:71][NH:72][CH:73]2[CH2:75][CH2:74]2)[CH2:46]1)=[O:44])([CH3:41])([CH3:40])[CH3:39].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CC#N>[C:38]([O:42][C:43]([N:45]1[CH2:49][C@@H:48]([CH2:50][N:51]([CH:68]([CH3:69])[CH3:70])[C:52](=[O:67])[C:53]2[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[C:55]([O:61][CH2:62][CH2:63][CH2:64][O:65][CH3:66])[CH:54]=2)[C@H:47]([CH2:71][N:72]([CH:73]2[CH2:74][CH2:75]2)[C:35](=[O:37])[CH2:34][C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([N+:25]([O-:27])=[O:26])[CH:29]=2)[CH2:46]1)=[O:44])([CH3:40])([CH3:41])[CH3:39]
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 5

HCID 8471TriethylamineHCID 158763-Nitrophenylacetic acidHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68616408(3R*,4R*)-3-Cyclopropylaminomethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 68618278(3R*,4R*)-3-({Cyclopropyl-[2-(3-nitro-phenyl)-acetyl]-amino}-methyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

At 0° C. HBTU (426 mg, 1.12 mmol) is added to a solution of 3-nitrophenylacetic acid (187 mg, 1.03 mmol) in CH3CN (10 mL) and the resulting solution is stirred for 10 min. Then a solution of (3R*,4R*)-3-cyclopropylaminomethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.2 g, 0.375 mmol). (500 mg, 0.94 mmol) and triethylamine (1.04 mL, 7.5 mmol) in CH3CN (10 mL) is added at 0° C. and the reaction mixture is stirred at RT for another 2 h. For workup a sat. solution of NaHCO3 is added and the mixture is extracted with ethyl acetate. Washing of the combined extracts with brine, drying (Na2SO4), filtration and evaporation of the solvent affords the crude product which is purified by flash chromatography on silica gel (eluent: CH2Cl2 to CH2Cl2/MeOH 9:1) to give the title compound. MS (LC-MS): 597.0 [M+H-Boc]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mumin): 6.47 min.

後処理

  1. customAt 0° C
  2. stirringthe reaction mixture is stirred at RT for another 2 h
  3. extractionthe mixture is extracted with ethyl acetate
  4. washWashing of the combined extracts with brine
  5. customdrying
  6. filtration(Na2SO4), filtration and evaporation of the solvent
  7. customaffords the crude product which
  8. customis purified by flash chromatography on silica gel (eluent: CH2Cl2 to CH2Cl2/MeOH 9:1)

出典と根拠

ORDレコード
ord-a925cdd059e0493ca4e04e3ee1862e1c
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07807709B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート