Methanol → HCID 10199719、化合物

HRID 1017643

反応式

HRID 1017643 の反応式
[C:1]([NH:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C1(OP(Cl)(OC2C=CC=CC=2)=O)C=CC=CC=1.[NH2:38][C@@H:39]1[CH:44]2[CH2:45][CH2:46][N:41]([CH2:42][CH2:43]2)[CH2:40]1.CO>C(Cl)Cl.CN(C=O)C>[N:41]12[CH2:46][CH2:45][CH:44]([CH2:43][CH2:42]1)[C@@H:39]([NH:38][C:14](=[O:16])[C:13]1[CH:12]=[CH:11][C:10]([O:9][C:8]3[CH:7]=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:20][CH:19]=3)=[CH:18][CH:17]=1)[CH2:40]2

参加物

7

反応物 4

HCID 887MethanolHCID 75654Diphenyl chlorophosphateHCID 719215(3R)-1-Azabicyclo(2.2.2)octan-3-amineHCID 36510794-(4-acetamidophenoxy)benzoic Acid

生成物 1

HCID 10199719HCID 10199719、化合物収率 39%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

TEA (130 μL, 1.0 mmol) is added to a suspension of the product of Step D (250 mg, 0.9 mmol) in CH2Cl2 (9 mL). Diphenylchlorophosphate (190 μL, 0.9 mmol) is added and the resulting solution is stirred at room temperature for 30 minutes. This solution is added to a solution of (R)-3-aminoquinuclidine (110 mg, 0.88 mmol) in DMF (1 mL). The resulting solution is stirred overnight at room temperature. MeOH is added and the mixture is poured through a column of AG50W×2 ion exchange resin (H+ form). The resin is washed with MeOH and then the product is eluted with 5% TEA in MeOH. The eluent is evaporated to dryness. The product is crystallized from CH3CN to yield the desired product (130 mg, 39%). MS for C22H25N3O3 (ESI) (M+H)+ m/z 380.

後処理

  1. stirringThe resulting solution is stirred overnight at room temperature
  2. additionthe mixture is poured through a column of AG50W×2 ion exchange resin (H+ form)
  3. washThe resin is washed with MeOH
  4. washthe product is eluted with 5% TEA in MeOH
  5. customThe eluent is evaporated to dryness
  6. customThe product is crystallized from CH3CN

出典と根拠

ORDレコード
ord-16cd78e5436f4f8fb843027ec0241c99
出典データセット
uspto-grants-2002_11
特許番号
US06479510B2

関連ノート

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