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

HRID 1401870노트

반응식

HRID 1401870 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
32.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c2ebfb40b954fc9b72c201de48a8ff3
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08907132B2

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