Benzylamine → (R)-N-Benzyl-2-acetamido-3-hydroxypropionamide

HRID 1401870ノート

反応式

HRID 1401870 の反応式
CN1CCOCC1.C(OC(Cl)=O)C(C)C.[C:16]([NH:19][C@H:20]([CH2:24][OH:25])[C:21]([OH:23])=O)(=[O:18])[CH3:17].[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[C:16]([NH:19][C@H:20]([CH2:24][OH:25])[C:21]([NH:33][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:23])(=[O:18])[CH3:17]

参加物

6

反応物 4

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 10844522N-Acetyl-D-serine

生成物 1

HCID 10889901(R)-N-Benzyl-2-acetamido-3-hydroxypropionamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
32.5 °C

実験手順

4-methylmorpholine (7.3 ml) followed by isobutylchloroformate (12.35 ml) was added to a suspension of (R)-2-acetamido-3-hydroxypropanoic acid (7 grams) in tetrahydrofuran (147 ml) at −78 to −75° C., benzylamine (10.4 ml) was added to it and the reaction mixture temperature was raised to 30-35° C. then stirred for 30 minutes. The reaction mixture was filtered and the filtrate was distilled off under reduced pressure. The obtained residue was dissolved in methylene chloride (35 ml) and washed with aqueous hydrochloric acid followed by sodium carbonate and then with water. The solvent from the methylene chloride layer was distilled off completely under reduced pressure to get the title compound.

後処理

  1. filtrationThe reaction mixture was filtered
  2. distillationthe filtrate was distilled off under reduced pressure
  3. dissolutionThe obtained residue was dissolved in methylene chloride (35 ml)
  4. washwashed with aqueous hydrochloric acid
  5. distillationThe solvent from the methylene chloride layer was distilled off completely under reduced pressure

出典と根拠

ORDレコード
ord-9c2ebfb40b954fc9b72c201de48a8ff3
出典データセット
uspto-grants-2014_12
特許番号
US08907132B2

反応ノート

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