Methanol → (-)-methyl 3-(5-cyanobenzo[d]oxazol-2-yl)-3-(5-methoxy-7-methyl-1H-indol-4-yl)propanoate

HRID 2174119노트

반응식

HRID 2174119 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([C:16]3[C:24]([O:25][CH3:26])=[CH:23][C:22]([CH3:27])=[C:21]4[C:17]=3[CH:18]=[CH:19][NH:20]4)[CH2:12][C:13]([OH:15])=[O:14])=[N:8][C:7]=2[CH:28]=1)#[N:2].CO.[CH2:31]1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([C:16]3[C:24]([O:25][CH3:26])=[CH:23][C:22]([CH3:27])=[C:21]4[C:17]=3[CH:18]=[CH:19][NH:20]4)[CH2:12][C:13]([O:15][CH3:31])=[O:14])=[N:8][C:7]=2[CH:28]=1)#[N:2]

참가 물질

6

반응물 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 86701761(+)-3-(5-cyanobenzo[d]oxazol-2-yl)-3-(5-methoxy-7-methyl-1H-indol-4-yl)propanoic acid

생성물 1

HCID 86701762(-)-methyl 3-(5-cyanobenzo[d]oxazol-2-yl)-3-(5-methoxy-7-methyl-1H-indol-4-yl)propanoate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of (±)-3-(5-cyanobenzo[d]oxazol-2-yl)-3-(5-methoxy-7-methyl-1H-indol-4-yl)propanoic acid (Example 148-B) (60 mg, 0.160 mmol) in DCM (639 μl) were added MeOH (16.17 μl, 0.400 mmol), DMAP (3.91 mg, 0.032 mmol) and DCC (52.8 mg, 0.256 mmol) successively. The reaction mixture was stirred at rt overnight. The reaction mixture was quenched with a saturated solution of ammonium chloride, diluted with DCM and water and passed through a phase separator. The organic layer was concentrated to give crude product that was purified via FCC with Heptane/AcOEt (100/0 to 0/100) to obtain the title compound. (ESI+) m/z 390.4 (M+H).

후처리

  1. customThe reaction mixture was quenched with a saturated solution of ammonium chloride
  2. additiondiluted with DCM and water
  3. concentrationThe organic layer was concentrated
  4. customto give crude product that
  5. customwas purified via FCC with Heptane/AcOEt (100/0 to 0/100)

출처 및 근거

ORD 기록
ord-8420210790544af3990d68aaf0a5c6da
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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