Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(4-chlorophenylamino)-2-phenylacetate

HRID 1255013

반응식

HRID 1255013 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:44]12[CH2:51][CH2:50][CH:47]([CH2:48][CH2:49]1)[C@@H:46](O)[CH2:45]2>C1COCC1>[N:44]12[CH2:51][CH2:50][CH:47]([CH2:48][CH2:49]1)[C@@H:46]([O:11][C:10](=[O:12])[CH:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:45]2

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 305145(4-Chloro-phenylamino)-phenyl-acetic acid

생성물 1

HCID 46840420(R)-quinuclidin-3-yl 2-(4-chlorophenylamino)-2-phenylacetate수율 37.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (4-chloro-phenylamino)-phenyl-acetic acid (I28) (574 mg, 2.20 mmol) in dry THF (20 mL), are added DCC (543 mg, 2.64 mmol), HOBt (359 mg, 2.64 mmol) and 3(R)-quinuclidinol (558 mg, 4.40 mmol). The resulting mixture is stirred at RT overnight (UPLC-MS monitoring: complete conversion). The solvent is evaporated and the residue is portitioned between EtOAc and 2M K2CO3. The organic phase is dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is purified by flash chromatography (DCM/MeOH=99/1 to 85/15) to obtain the title compound as a white solid (306 mg, 37% yield, mixture of diastereoisomers).

후처리

  1. customThe solvent is evaporated
  2. dry with materialThe organic phase is dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe resulting crude is purified by flash chromatography (DCM/MeOH=99/1 to 85/15)

출처 및 근거

ORD 기록
ord-d1968f56a69f40a79b67a9d97a3e17f9
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455646B2

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