Citric Acid → HCID 57572194、化合物

HRID 602135ノート

反応式

HRID 602135 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10](NC)=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([N:23]1[CH2:31][CH2:30][CH2:29][CH:25]([C:26](O)=[O:27])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].O.O[N:34]1[C:38]2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[C:16]([O:20][C:21]([N:23]1[CH2:31][CH2:30][CH2:29][CH:25]([C:26]([NH:34][CH2:38][C:10]2[S:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:12][C:11]=2[CH3:13])=[O:27])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]

参加物

8

反応物 6

HCID 311Citric AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 672668402-(4-Chlorophenyl)-4-methylthiazol-5-yl methylamine

生成物 1

HCID 57572194HCID 57572194、化合物収率 101.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-(4-Chlorophenyl)-4-methylthiazol-5-yl methylamine (477 mg, 2.00 mmol), 1-tert-butoxycarbonyl nipecotic acid (459 mg, 2.00 mmol) and 1-hydroxybenzotriazole monohydrate (368 mg, 2.40 mmol) were dissolved in N,N-dimethylformamide (10 mL). While this mixture was chilled in an ice bath, 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (460 mg, 2.40 mmol) and N-methylmorpholine (0.484 mL, 4.40 mmol) were added. The mixture was then stirred at room temperature for 6 hours. Subsequently, 5% aqueous citric acid was added and the mixture was extracted with ethyl acetate. The extract washed sequentially with a saturated aqueous sodium bicarbonate solution and brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=5:1->1:1) gave 916 mg (100%) of the desired compound as a colorless powder.

後処理

  1. temperatureWhile this mixture was chilled in an ice bath
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract washed sequentially with a saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  5. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=5:1->1:1)

出典と根拠

ORDレコード
ord-97e81394ce7748fda324e712d980606a
出典データセット
uspto-grants-2011_03
特許番号
US07902367B2

反応ノート

読み込み中…