Triethylamine → Tert-butyl (s)-(2-(methoxy(methyl)amino)-2-oxo-1-phenylethyl)carbamate

HRID 588115노트

반응식

HRID 588115 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:20][NH:21][O:22][CH3:23].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([N:21]([O:22][CH3:23])[CH3:20])=[O:12])([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11010409(2S)-2-(((tert-butoxy)carbonyl)amino)-2-phenylacetic acid

생성물 1

HCID 10968398Tert-butyl (s)-(2-(methoxy(methyl)amino)-2-oxo-1-phenylethyl)carbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (S)-2-((tert-butoxycarbonyl)amino)-2-phenylacetic acid (1.0 g, 4.0 mmol) in dichloromethane (10 mL) were added N,O-dimethyl hydroxylamine hydrochloride (0.77 g, 8.0 mmol), EDCl (1.2 g, 6.0 mmol), HOBt (0.05 g, 0.4 mmol), Et3N (0.8 g, 8.0 mmol) and the contents were stirred at ambient temperature. After 2 hr, the reaction was quenched with ice cold H2O (10 mL), and the organic contents were extracted with CH2Cl2 (2×30 mL). The combined organic extracts were washed with brine (1×20 mL), dried over Na2SO4, concentrated and the residue thus obtained was purified by flash column chromatography to afford (S)-tert-butyl(2-(methoxy(methyl)amino)-2-oxo-1-phenylethyl)carbamate. 1H NMR (300 MHz, CDCl3) δ 7.39-7.29 (m, 5H), 5.77 (bs, 1H), 5.73 (bs, 1H), 3.47 (s, 3H), 3.20 (s, 3H), 1.42 (s, 9H).

후처리

  1. customthe reaction was quenched with ice cold H2O (10 mL)
  2. extractionthe organic contents were extracted with CH2Cl2 (2×30 mL)
  3. washThe combined organic extracts were washed with brine (1×20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customthe residue thus obtained
  7. customwas purified by flash column chromatography

출처 및 근거

ORD 기록
ord-02752db473984a81b2f17d9166cdab39
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226922B2

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