1,2-Dichloroethane → (R)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate

HRID 2201045노트

반응식

HRID 2201045 반응식
[C:1]([NH:11][C@@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1C=C2[N:29]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[NH2:29][C:20](=[O:22])[C@H:12]([NH:11][C:1](=[O:2])[O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 675678N-(Benzyloxycarbonyl)-D-phenylalanineHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 68077307(R)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate수율 91.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-Cbz-D-phenylalanine (1.00 g, 3.34 mmol) and HOBt hydrate (0.614 g, 4.01 mmol) in DMF (9 mL), EDC (0.834 g, 4.34 mmol) was added. The mixture was stirred for 40 min. Then conc. NH4OH (1.00 mL, ˜14 mmol) was added. It was stirred for 72 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-benzyl 1-amino-1-oxo-3-phenylpropan-2-ylcarbamate as a solid (0.910 g).

후처리

  1. stirringIt was stirred for 72 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-4d2e2998707c488986807568655e45c3
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359375B2

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