4-Methylmorpholine → Benzyl (2R)-2-Benzyl-3-thiazol-4-ylpropionate

HRID 973501ノート

反応式

HRID 973501 の反応式
[CH2:1]([C@H:8]([CH2:19][C:20]([CH2:22]Cl)=O)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]([NH2:26])=[S:25].CN1CCOCC1>CC(C)=O.CCOCC>[CH2:1]([C@H:8]([CH2:19][C:20]1[N:26]=[CH:24][S:25][CH:22]=1)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 79724-MethylmorpholineHCID 3005587MethanethioamideHCID 10449338Benzyl (2R)-2-Benzyl-3-chloromethylcarbonylpropionate

生成物 1

HCID 15018104Benzyl (2R)-2-Benzyl-3-thiazol-4-ylpropionate収率 76%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 3283Diethyl Ether溶媒

実験手順

The resultant compound from Example 34 (476.8 mg, 1.44 mmol) and thioformamide (176 mg, 2.88 mmol) in acetone (6 ml) were stirred at room temperature for 108 h. N-methylmorpholine (0.16 ml, 1.40 mmol) was added and after 20 min the mixture was diluted with ether, filtered, evaporated, and chromatographed on silica gel with 20% ethyl acetate in hexane to afford 369 mg (76%) of an oil. 1H NMR (CDCl3) δ8.70 (d,1H), 7.05-7.35 (m,10H), 6.90 (d,1H), 5.00 (d,1H), 4.95 (d,1H), 3.28-3.35 (m,1H), 3.19 (dd,1H), 2.95-3.10 (m,2H), 2.88 (dd,1H).

後処理

  1. filtrationfiltered
  2. customevaporated
  3. customchromatographed on silica gel with 20% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-811b13b68f8144ab849148ce71fd67f0
出典データセット
uspto-grants-1991_11
特許番号
US05063208

反応ノート

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