1,2-Dichloroethane → 8-Methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenyl-2-(phenylamino)acetate

HRID 76970

反応式

HRID 76970 の反応式
[C:1]1([CH:7]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:32][N:33]1[CH:38]2[CH2:39][CH2:40][CH:34]1[CH2:35][CH:36](O)[CH2:37]2>CN(C=O)C>[C:1]1([CH:7]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([O:10][CH:36]2[CH2:37][CH:38]3[N:33]([CH3:32])[CH:34]([CH2:40][CH2:39]3)[CH2:35]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 19375alpha-(Phenylamino)benzeneacetic acidHCID 757711-Hydroxybenzotriazole

生成物 1

HCID 468412398-Methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenyl-2-(phenylamino)acetate収率 7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-phenyl-2-(phenylamino)acetic acid I1 (250 mg, 0.90 mmol), EDC (255 mg, 1.35 mmol), HOBt (245 mg, 1.80 mmol) and 8-methyl-8-azabicyclo[3.2.1]octan-3-ol (380 mg, 2.71 mmol) in dry DMF (10 mL) is heated under microwave irradiation at 100° C. for 1 hour (LC-MS monitoring: complete conversion). The reaction is concentrated under reduced pressure and the residue is portioned between EtOAc and water. The organic phase is dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is purified by preparative HPLC. The collected compound is partitioned between 1N NaHCO3 and DCM, the organic phase is separated dried over Na2SO4, filtered and evaporated under vacuum to give 20.1 mg of the title compound as a colorless oil (7% yield, mixture of diastereoisomers).

後処理

  1. concentrationThe reaction is concentrated under reduced pressure
  2. dry with materialThe organic phase is dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe resulting crude is purified by preparative HPLC
  6. customThe collected compound is partitioned between 1N NaHCO3 and DCM
  7. customthe organic phase is separated
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated under vacuum

出典と根拠

ORDレコード
ord-f10d5d05994e455c820c91ae1f7dab49
出典データセット
uspto-grants-2014_09
特許番号
US08835682B2

関連ノート

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