Ethoxyacetic acid → tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-{[(ethoxyacetyl)amino]methyl}-1,4-oxazepane-4-carboxylate

HRID 1022628

反応式

HRID 1022628 の反応式
[NH2:1][CH2:2][C@H:3]1[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([F:17])[CH:11]=2)[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1.[CH2:25]([O:27][CH2:28][C:29](O)=[O:30])[CH3:26].N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C1COCC1.C(N(CC)CC)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C@@H:9]2[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4][C@H:3]2[CH2:2][NH:1][C:29](=[O:30])[CH2:28][O:27][CH2:25][CH3:26])=[CH:11][C:12]=1[F:17]

参加物

7

反応物 4

HCID 12301Ethoxyacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66975002tert-butyl (6R,7R)-6-(aminomethyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate

生成物 1

HCID 66975262tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-{[(ethoxyacetyl)amino]methyl}-1,4-oxazepane-4-carboxylate収率 83.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of tert-butyl (6R,7R)-6-(aminomethyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate (150 mg), ethoxyacetic acid (35 mg), 1H-benzotriazol-1-ol (67.8 mg) and triethylamine (0.146 ml) in THF (2.1 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (96 mg), and the mixture was stirred overnight. To the reaction mixture was added distilled water, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (125 mg).

後処理

  1. additionTo the reaction mixture was added
  2. distillationdistilled water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with distilled water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-eac980e094d04dc183f4ad69722e3411
出典データセット
uspto-grants-2014_05
特許番号
US08722662B2

関連ノート

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