Methanol → N-[2-(8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepin-10-yl)-2-oxoethyl]-3-[(2-furanylmethyl)thio]propanamide

HRID 248824ノート

反応式

HRID 248824 の反応式
C[Al](C)C.[O:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][S:11][CH2:12][CH2:13][C:14]([O:16]C)=O.[NH2:18][CH2:19][C:20]([N:22]1[CH2:28][C:27]2[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=2[O:25][C:24]2[CH:33]=[CH:34][C:35]([Cl:37])=[CH:36][C:23]1=2)=[O:21].CO>C1(C)C=CC=CC=1>[Cl:37][C:35]1[CH:34]=[CH:33][C:24]2[O:25][C:26]3[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=3[CH2:28][N:22]([C:20](=[O:21])[CH2:19][NH:18][C:14](=[O:16])[CH2:13][CH2:12][S:11][CH2:10][C:6]3[O:5][CH:9]=[CH:8][CH:7]=3)[C:23]=2[CH:36]=1

参加物

6

反応物 4

HCID 887MethanolHCID 1066106110-(Aminoacetyl)-8-chloro-10,11-dihydrodibenz-[b,f][1,4]oxazepineHCID 15225386Methyl 3-(furfurylthio)propionateHCID 16682925Trimethylaluminum

生成物 1

HCID 9933776N-[2-(8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepin-10-yl)-2-oxoethyl]-3-[(2-furanylmethyl)thio]propanamide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Trimethylaluminum (2.0M in toluene; 4.6 mL) was added dropwise via syringe to a stirred solution of methyl 3-[(2-furanylmethyl)thio]propanoate (0.75 gram) and 10-(aminoacetyl)-8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine (1.00 gram) in toluene (30 mL) at room temperature under nitrogen, and the reaction was stirred for 5 hours. Methanol (14 mL) was then added, and the reaction was stirred at room temperature overnight. The reaction was evaporated in vacuo, and the resulting orange residue was partitioned between chloroform (50 mL) and 1N NaOH (50 mL). The layers were separated and the aqueous layer was extracted with chloroform (50 mL). The combined chloroform extracts were washed with 1N NaOH (50 mL), 1N HCl (2×50 mL), and brine (50 mL), dried over MgSO4, and evaporated in vacuo. The crude product was purified by flash chromatography through silica gel 60 (350 mL) using 3:1 chloroform:ethyl acetate followed by recrystallization from cyclohexane/ethyl acetate. The yield of the title compound was 0.63 gram (40%) in the form of a tan solid. Analysis calculated for C23H21ClN2O4S: C, 60.46; H, 4.63; N, 6.13; Cl, 7.67; S, 7.02. Found: C, 60.16; H, 4.62; N, 6.05; Cl, 8.06; S, 7.02. DSC: 90°-95° C.

後処理

  1. stirringthe reaction was stirred at room temperature overnight
  2. customThe reaction was evaporated in vacuo
  3. customthe resulting orange residue was partitioned between chloroform (50 mL) and 1N NaOH (50 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with chloroform (50 mL)
  6. washThe combined chloroform extracts were washed with 1N NaOH (50 mL), 1N HCl (2×50 mL), and brine (50 mL)
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuo
  9. customThe crude product was purified by flash chromatography through silica gel 60 (350 mL)
  10. customethyl acetate followed by recrystallization from cyclohexane/ethyl acetate
  11. custom90°-95° C.

出典と根拠

ORDレコード
ord-45e8eade1d9b4d509bac4c104022c219
出典データセット
uspto-grants-1993_05
特許番号
US05212169

反応ノート

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