Diisopropylethylamine → ((4R)-1-{[3-(4-methylphenyl)isoxazol-4-yl]carbonyl}-4-phenylpyrrolidin-3-yl)methanol

HRID 1446285

반응식

HRID 1446285 반응식
[C:1]1([CH:7]2[CH2:11][NH:10][CH2:9][CH:8]2[CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH3:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]2[C:56]([C:57](O)=[O:58])=[CH:55][O:54][N:53]=2)=[CH:48][CH:47]=1>CN(C=O)C>[CH3:45][C:46]1[CH:47]=[CH:48][C:49]([C:52]2[C:56]([C:57]([N:10]3[CH2:11][C@@H:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:8]([CH2:12][OH:13])[CH2:9]3)=[O:58])=[CH:55][O:54][N:53]=2)=[CH:50][CH:51]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 13316928(4-Phenylpyrrolidin-3-yl)methanolHCID 588287973-(4-Methylphenyl)isoxazole-4-carboxylic acid

생성물 1

HCID 68687311((4R)-1-{[3-(4-methylphenyl)isoxazol-4-yl]carbonyl}-4-phenylpyrrolidin-3-yl)methanol수율 41.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of (4-phenylpyrrolidin-3-yl)methanol (7 mg, 0.033 mmol), TBTU (13 mg, 0.039 mmol, 1.2 equ.) and N-ethyl-N-isopropylpropan-2-amine (11 μL, 0.066 mmol, 2 equ.) in DMF (0.3 mL) was added to 3-(4-methylphenyl)isoxazole-4-carboxylic acid (7 mg, 0.033 mmol) and the reaction mixture was stirred at rt for 2 h. The solvent was evaporated and the crude product was purified by RP-HPLC. After evaporation of the solvents the product was dried in vacuum to yield the title compound (5 mg). MS (ESI, pos. ion) m/z calcd for C22H22N2O3: 362.1630, found 362.1624.

후처리

  1. customThe solvent was evaporated
  2. customthe crude product was purified by RP-HPLC
  3. customAfter evaporation of the solvents the product
  4. customwas dried in vacuum

출처 및 근거

ORD 기록
ord-50997e44bcbd46cb96bd88a24ba86e50
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666888B2

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