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

HRID 1044041

반응식

HRID 1044041 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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:10]([O:12][C@@H:46]2[CH:47]3[CH2:50][CH2:51][N:44]([CH2:49][CH2:48]3)[CH2:45]2)=[O:11])=[CH:4][CH:3]=1

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 2-(4-chlorophenylamino)-2-phenylacetic acid (I11) (574 mg, 2.20 mmol) in dry THF (20 ml), were 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 was stirred at RT overnight (UPLC-MS monitoring: complete conversion). The solvent was evaporated, and the residue was partitioned between EtOAc and 2M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The resulting crude was purified by flash chromatography (DCM/MeOH=99/1 to 85/15) to obtain the title compound (306 mg, 37% yield, mixture of diastereomers).

후처리

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between EtOAc and 2M K2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe resulting crude was purified by flash chromatography (DCM/MeOH=99/1 to 85/15)

출처 및 근거

ORD 기록
ord-73fcd8624b4848568cea578149a9d504
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563577B2

연결된 노트

불러오는 중…