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

HRID 588115ノート

反応式

HRID 588115 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-02752db473984a81b2f17d9166cdab39
出典データセット
uspto-grants-2016_01
特許番号
US09226922B2

反応ノート

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