1,2-Dichloroethane → tert-Butyl (1R)-2-amino-1-(1H-indol-3-ylmethyl)-2-oxoethylcarbamate

HRID 84876

반응식

HRID 84876 반응식
[C:1]([NH:8][C@@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[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:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 111050N-((tert-Butoxy)carbonyl)-D-tryptophanHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 57107549tert-Butyl (1R)-2-amino-1-(1H-indol-3-ylmethyl)-2-oxoethylcarbamate수율 96.5%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of N-Boc-D-tryptophan (1.00 g, 3.29 mmol), HOBt monohydrate (0.600 g, 3.92 mmol) and EDC (0.820 g, 4.27 mmol) in DMF (12 mL) was stirred at room temperature for 2 h, conc. NH4OH (1.10 mL, ca. 15.4 mmol) was added. The mixture 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-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate (0.963 g)

후처리

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

출처 및 근거

ORD 기록
ord-509d55ba440a4679bebd17fc86ac137c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846928B2

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