Diisopropylethylamine → tert-Butyl 4-(2-oxobenzo[d]oxazol-3(2H)-yl)piperidine-1-carboxylate

HRID 1377683ノート

反応式

HRID 1377683 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Cl[C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][C:32]2=[O:34])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 22380697tert-Butyl 4-(2-hydroxyanilino)piperidine-1-carboxylate

生成物 1

HCID 22644594tert-Butyl 4-(2-oxobenzo[d]oxazol-3(2H)-yl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred 0° C. solution of 1-t-Butyloxycarbonyl-4-(2-hydroxyphenylamino)piperidine (3.0 g, 10 mmol) from Step 1 of Example 41 in dry THF (40 mL) was added DIEA (5.2 mL, 30 mmol), followed by triphosgene (1.08 g, 3.60 mmol). After 30 min, the reaction was warmed to ambient temperature and stirred for 24 h. The precipitated hydrochloride salt of DIEA was removed by filtration and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with saturated aqueous NaHCO3 (2×100 mL), water (100 mL), 5% aqueous citric acid (100 mL), and brine (100 mL). The EtOAc layer was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. 3-(1-t-Butyloxycarbonyl-4-piperidinyl)benzoxazolidin-2-one was obtained as a solid (82% yield).

後処理

  1. customThe precipitated hydrochloride salt of DIEA was removed by filtration
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (200 mL)
  4. washwashed with saturated aqueous NaHCO3 (2×100 mL), water (100 mL), 5% aqueous citric acid (100 mL), and brine (100 mL)
  5. dry with materialThe EtOAc layer was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-f43796f42a1a401b8fccf112ec120068
出典データセット
uspto-grants-1997_09
特許番号
US05665719

反応ノート

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