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Diisopropylethylamine → 5-(S)-azidomethyl-3-[4'-(N-methoxyamino)carbonyl-3'-fluorophenyl]-oxazolidine-2-one

HRID 351875
ノート
印刷プレビュー

反応式

HRID 351875 の反応式
Cl.[CH3:2][O:3][NH2:4].[N:5]([CH2:8][C@H:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21](OC3C(F)=C(F)C(F)=C(F)C=3F)=[O:22])=[C:17]([F:35])[CH:16]=2)[CH2:10]1)=[N+:6]=[N-:7].C(N(C(C)C)CC)(C)C>C1COCC1>[N:5]([CH2:8][C@H:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:4][O:3][CH3:2])=[O:22])=[C:17]([F:35])[CH:16]=2)[CH2:10]1)=[N+:6]=[N-:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 229662165-(S)-Azidomethyl-3-[4'-(pentafluorophenoxy)carbonyl-3'-fluorophenyl]-oxazolidine-2-one

生成物 1

HCID 229662155-(S)-azidomethyl-3-[4'-(N-methoxyamino)carbonyl-3'-fluorophenyl]-oxazolidine-2-one収率 83.3%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

N-Methoxyamine hydrochloride (123 mg, 1.5 mmol) was added to a solution of 5-(S)-azidomethyl-3-[4′-(pentafluorophenoxy)carbonyl-3′-fluorophenyl]-oxazolidine-2-one (600 mg, 1.3 mmol) and diisopropylethylamine (0.26 ml, 1.5 mmol) in THF (8 ml), and the mixture stirred overnight at r.t. Solvent was removed under vacuum, and ethyl acetate with 3% aq. citric acid added. Organic layer was washed twice with 3% citric acid, brine, and dried (Na2SO4). Solvent was removed under vacuum, and the crude material crystallized from ethanol-ether to give a white crystalline product (335 mg, 83%). HPLC Rt=4.8. MS (m/z): [M+H]+=310.

後処理

  1. customSolvent was removed under vacuum, and ethyl acetate with 3% aq. citric acid
  2. additionadded
  3. washOrganic layer was washed twice with 3% citric acid, brine
  4. dry with materialdried (Na2SO4)
  5. customSolvent was removed under vacuum
  6. customthe crude material crystallized from ethanol-ether

出典と根拠

ORDレコード
ord-5a53b491230843f3b00c45f05d7b44b4
出典データセット
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06743811B2

反応ノート

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