Dicyclohexylcarbodiimide → HCID 67607091, 화합물

HRID 1619528노트

반응식

HRID 1619528 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=NC1CCCCC1)=NC1CCCCC1.N1(O)C2C=CC=CC=2N=N1.[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47](O)[CH2:46]2>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:10]([O:12][C@@H:47]1[CH:48]2[CH2:51][CH2:52][N:45]([CH2:50][CH2:49]2)[CH2:46]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 27567812-(((Tert-butoxy)carbonyl)amino)-2-(4-chlorophenyl)acetic acid

생성물 1

HCID 67607091HCID 67607091, 화합물수율 44.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)acetic acid (I46) (2.17 g, 7.58 mmol) in dry THF (70 ml), were added N,N′-methanediylidenedicyclohexanamine (1.88 g, 9.10 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (1.23 g, 9.10 mmol), and (R)-quinuclidin-3-ol (1.16 g, 9.10 mmol). The reaction was stirred at RT for 15 hours, and the solvent was evaporated. The residue was taken up with DCM, the insoluble solid was filtered off, and the organic solution was washed twice with aq. Na2CO3 and then brine, dried over Na2SO4 and evaporated. The crude was purified by flash chromatography (EtOAc/MeOH=8/2 to 85/15) to obtain (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)acetate (1.33 g; 44% yield).

후처리

  1. customthe solvent was evaporated
  2. filtrationthe insoluble solid was filtered off
  3. washthe organic solution was washed twice with aq. Na2CO3
  4. dry with materialbrine, dried over Na2SO4
  5. customevaporated
  6. customThe crude was purified by flash chromatography (EtOAc/MeOH=8/2 to 85/15)

출처 및 근거

ORD 기록
ord-e18b17fc78854c1293b2cd19598ff94a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772314B2

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