Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(benzyloxycarbonylamino)-2-phenylacetate

HRID 1619512노트

반응식

HRID 1619512 반응식
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:22]12[CH2:29][CH2:28][CH:25]([CH2:26][CH2:27]1)[C@@H:24](O)[CH2:23]2.C(=NC1CCCCC1)=NC1CCCCC1.N1(O)C2C=CC=CC=2N=N1>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([O:15][C@@H:24]1[CH:25]2[CH2:28][CH2:29][N:22]([CH2:27][CH2:26]2)[CH2:23]1)=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 98996(((Phenylmethoxy)carbonyl)amino)phenylacetic acid

생성물 1

HCID 67605836(R)-quinuclidin-3-yl 2-(benzyloxycarbonylamino)-2-phenylacetate수율 78.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-(benzyloxycarbonylamino)-2-phenylacetic acid (I28) (855 mg, 3.00 mmol) in THF (20 ml), were added (R)-quinuclidin-3-ol (457 mg, 3.60 mmol), N,N′-methanediylidenedicyclohexanamine (742 mg, 3.60 mmol) and 1H-benzo[d][1,2,3]triazol-1-ol (486 mg, 3.60 mmol). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The residue was taken up with DCM, the insoluble solid was filtered off, and the clear solution was washed twice with Na2CO3 and brine, dried over Na2SO4 and evaporated. The resulting crude is purified by silica gel flash chromatography (DCM/MeOH=9/1) to obtain (R)-quinuclidin-3-yl 2-(benzyloxy-carbonylamino)-2-phenylacetate (925 mg; 78% yield).

후처리

  1. customthe solvent was evaporated
  2. filtrationthe insoluble solid was filtered off
  3. washthe clear solution was washed twice with Na2CO3 and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe resulting crude is purified by silica gel flash chromatography (DCM/MeOH=9/1)

출처 및 근거

ORD 기록
ord-af62e90bd8ca47eabd6401c723859006
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772314B2

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