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Benzylamine → N-Benzyl 2-(Carbobenzyloxyamino)-3-Methoxypropionamide

HRID 1882739
ノート
印刷プレビュー

反応式

HRID 1882739 の反応式
[C:1]([NH:11][CH:12]([CH2:16][O:17][CH3:18])[C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O1CCCC1>[CH2:34]([NH:41][C:13](=[O:15])[CH:12]([NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH2:16][O:17][CH3:18])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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 7504BenzylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 123447572-([(Benzyloxy)carbonyl]amino)-3-methoxypropanoic acid

生成物 1

HCID 23509063N-Benzyl 2-(Carbobenzyloxyamino)-3-Methoxypropionamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

実験手順

A solution of 11 (0.52 g, 2.04 mmol) in dry tetrahydrofuran (10 mL) was cooled to −78° C. in a dry ice-acetone bath under a N2 atmosphere. To this was added via a dry syringe 4-methylmorpholine (0.34 mL, 3.06 mmol). After stirring for 5 minutes, isobutyl chloroformate (0.4 mL, 3.06 mmol) was added via dry syringe and then the mixture stirred for 5 minutes. This was followed by the addition of benzylamine (0.32 mL, 3.06 mmol). After stirring at −78° C. for 5 minutes, the reaction was allowed to warm to room temperature, and stirring was continued at room temperature (30 min). The hydrochloride salt of 4-methyl morpholine was removed from the reaction by filtration. The clear filtrate was evaporated in vacuo and the residue was triturated with ethyl ether (5.0 mL). The white crystalline product obtained was isolated by filtration after washing with small amounts of ether and air-dried (0.55 g, 78%): mp 112°-114° C., Rf 0.6 (10% MeOH/CHCl3)

後処理

  1. customvia dry syringe
  2. stirringthe mixture stirred for 5 minutes
  3. stirringAfter stirring at −78° C. for 5 minutes
  4. stirringstirring
  5. customwas continued at room temperature
  6. custom(30 min)
  7. customThe hydrochloride salt of 4-methyl morpholine was removed from the reaction by filtration
  8. customThe clear filtrate was evaporated in vacuo
  9. customthe residue was triturated with ethyl ether (5.0 mL)
  10. customThe white crystalline product obtained
  11. customwas isolated by filtration
  12. washafter washing with small amounts of ether
  13. customair-dried (0.55 g, 78%)

出典と根拠

ORDレコード
ord-ce0a20d96aa04cbe8878ab16f826c0c8
出典データセット
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
USRE038551E1

反応ノート

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