1,2-Dichloroethane → (R)-tert-butyl 1-amino-3-(benzyloxy)-1-oxopropan-2-ylcarbamate

HRID 2201049

반응식

HRID 2201049 반응식
[C:1]([NH:8][C@@H:9]([C:19]([OH:21])=O)[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=C2[N:28]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[NH2:28][C:19](=[O:21])[C@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 2733693(R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acidHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 7216902(R)-tert-butyl 1-amino-3-(benzyloxy)-1-oxopropan-2-ylcarbamate수율 87.7%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-Boc-O-benzyl-D-serine (510 mg, 1.72 mmol) and HOBt hydrate (317 mg, 2.07 mmol) in DMF (9 mL), EDC (432 mg, 2.25 mmol) was added. The mixture was stirred for 60 min. Then conc. NH4OH (0.600 mL, ˜8.40 mmol) was added. It was stirred for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-tert-butyl 1-amino-3-(benzyloxy)-1-oxopropan-2-ylcarbamate (444 mg).

후처리

  1. stirringIt was stirred for 18 h
  2. customThe organic phase was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1003d443af964ada8ae07771af917bb3
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359375B2

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