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

HRID 2174119ノート

反応式

HRID 2174119 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8420210790544af3990d68aaf0a5c6da
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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