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Morpholine → N-[N-benzyloxycarbonyl-L-prolyl]morpholine

HRID 429753
ノート
印刷プレビュー

反応式

HRID 429753 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 101987Benzyloxycarbonyl-L-proline

生成物 1

HCID 13564348N-[N-benzyloxycarbonyl-L-prolyl]morpholine収率 69.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

実験手順

A solution of N-benzyloxycarbonyl-L-proline (5 g, 20.06 mmol), morpholine (1.92 ml, 20.06 mmol), and N-hydroxysuccinimide (2.31 g, 20.06 mmol) in N, N-dimethylformamide (100 ml) was added DCC (4.14 g, 20.06 mmol) and the resulting mixture was stirred for 4 h at room temperature. After the precipitation was filtered off, the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate and the resulting precipitation was filtered off. After the filtrate was washed with dilute hydrochloric acid, saturated sodium hydrogencarbonate aq., and water, the organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was crystallized from the mixed solvents of ethyl acetate-hexane to give the compound (34) (4.44 g, 69.5%).

後処理

  1. customAfter the precipitation
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. customthe resulting precipitation
  6. filtrationwas filtered off
  7. washAfter the filtrate was washed with dilute hydrochloric acid, saturated sodium hydrogencarbonate aq., and water
  8. dry with materialthe organic layer was dried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was crystallized from the mixed solvents of ethyl acetate-hexane

出典と根拠

ORDレコード
ord-918a80e19f184c84a99dbd9be477e862
出典データセット
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06319902B1

反応ノート

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