Triethylamine → Methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-(4-hydroxyphenyl)acetate

HRID 454970

反応式

HRID 454970 の反応式
Cl.[CH3:2][O:3][C:4](=[O:13])[C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:6].[C:14](=O)([O-:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O:23]C(C)(C)C.C(N(CC)CC)C>O1CCCC1>[CH3:2][O:3][C:4](=[O:13])[C@H:5]([NH:6][C:14]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([OH:23])=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 12247453D-Phenylglycine methyl ester hydrochlorideHCID 52911111Di-tert-butyl di-carbonate

生成物 1

HCID 10934864Methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-(4-hydroxyphenyl)acetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

(R)-(−)-2-phenylglycine methyl ester hydrochloride (2.17 g, 10 mmol) and di-t-butyl di-carbonate (2.62 g, 12 mmol) were combined in tetrahydrofuran (100 ml). Triethylamine (1.60 ml, 22 mmol) was added to the mixture via syringe at room temperature. The reaction mixture was stirred at room temperature overnight. The THF in reaction mixture was then removed in vacuum. Saturated aqueous NH4Cl and ethyl acetate were added to the mixture in a separatory funnel. The aqueous layer was extracted with ethyl acetate (3×40 ml). The combined organic layer was washed with saturated aqueous NH4Cl, dried over MgSO4, filtered and concentrated to give a white solid (3.08 g, crude product): 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.20 (d, J=8.1 Hz, 2H), 6.77 (m, 2H), 5.73 (br. s., 1H), 5.56 (br. s., 1H), 5.25 (d, J=6.6 Hz, 1H), 3.73 (s, 3H), 1.46 (s, 9H) LCMS (ESI) m/e 282.1 [(M+H)+, calcd for C14H20NO5 282.3].

後処理

  1. customwas then removed in vacuum
  2. additionSaturated aqueous NH4Cl and ethyl acetate were added to the mixture in a separatory funnel
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×40 ml)
  4. washThe combined organic layer was washed with saturated aqueous NH4Cl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a white solid (3.08 g, crude product)

出典と根拠

ORDレコード
ord-3ca3b1e1dee741089f826942e7eb8ff0
出典データセット
uspto-grants-2013_07
特許番号
US08497271B2

関連ノート

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