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1,2-Dichloroethane → (R)-tert-butyl 1-amino-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate

HRID 332794
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HRID 332794 반응식
[C:1]([NH:8][C@@H:9]([C:16]([OH:18])=O)[CH2:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=C2[N:25]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[NH2:25][C:16](=[O:18])[C@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH2:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1
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참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7017898Boc-D-2-thienylalanine

생성물 1

HCID 67776928(R)-tert-butyl 1-amino-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate수율 89.1%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

실험 절차

A solution of Boc-β-(2-thienyl)-D-alanine (504 mg, 1.86 mmol), HOBt hydrate (340 mg, 2.22 mmol) and EDC (460 mg, 2.39 mmol) in DMF (8 mL) was stirred at room temperature for 30 min. Conc. NH4OH (0.800 mL) was added. The mixture was stirred at room temperature for 20 h. Water and EtOAc were added. Organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-tert-butyl 1-amino-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate as a solid (448 mg).

후처리

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

출처 및 근거

ORD 기록
ord-5f416669ae574e3584c5449ea663b0f1
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08877760B2

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