4-Methylmorpholine → N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester 4-piperidinamide

HRID 1018462

反応式

HRID 1018462 の反応式
[CH2:1]([O:8][C:9](=[O:23])[C@H:10]([CH2:19][C:20]([OH:22])=[O:21])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.CN1CCOCC1.C[N:38]([C:40]([O:44]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C>[CH2:1]([O:8][C:9](=[O:23])[C@H:10]([CH2:19][C:20]([OH:22])=[O:21])[NH:11][C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][CH:27]([C:40]([NH2:38])=[O:44])[CH2:26][CH2:25]1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 8082PiperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7017887(3S)-4-(benzyloxy)-3-(((tert-butoxy)carbonyl)amino)-4-oxobutanoic acid

生成物 1

HCID 70086528N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester 4-piperidinamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester (1 g) and piperidine (0.32 mL) in acetonitrile (15 mL) was allowed to react with N-methylmorpholine (0.42 mL) and TBTU (1.2 g) for 6 hr at room temperature. The solvent was removed and the residue, dissolved in EtOAc, was sequentially washed with 2% aqueous hydrochloric acid, saturated aq. NaHCO3 and brine. After drying (Na2SO4) and rotoevaporation, the resulting yellowish oil was purified by flash chromatography over silica to obtain N-(tert-butoxycarbonyl)-L-aspartic acid 1-benzyl ester-4-piperidinamide (900 mg) as a colorless oil.

後処理

  1. customThe solvent was removed
  2. dissolutionthe residue, dissolved in EtOAc
  3. washwas sequentially washed with 2% aqueous hydrochloric acid, saturated aq. NaHCO3 and brine
  4. dry with materialAfter drying (Na2SO4) and rotoevaporation
  5. customthe resulting yellowish oil was purified by flash chromatography over silica

出典と根拠

ORDレコード
ord-60c005376dde4530a849137725f3e1dc
出典データセット
uspto-grants-2002_11
特許番号
US06482827B1

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