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Tert-butoxycarbonylalanine → [(S)-1-(3-Bromo-2-cyclopropylamino-4-fluorophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester

HRID 243139
ノート
印刷プレビュー

反応式

HRID 243139 の反応式
[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH2:9])[C:3]=1[NH:10][CH:11]1[CH2:13][CH2:12]1.[C:14]([O:18][C:19]([NH:21][C@@H:22]([CH3:26])[C:23](O)=[O:24])=[O:20])([CH3:17])([CH3:16])[CH3:15].C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:14]([O:18][C:19](=[O:20])[NH:21][C@H:22]([C:23](=[O:24])[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Br:1])[C:3]=1[NH:10][CH:11]1[CH2:13][CH2:12]1)[CH3:26])([CH3:15])([CH3:16])[CH3:17]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 681575913-Bromo-N2-cyclopropyl-4-fluorobenzene-1,2-diamine

生成物 1

HCID 68158397[(S)-1-(3-Bromo-2-cyclopropylamino-4-fluorophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester収率 81.4%

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A mixture of 3-bromo-N2-cyclopropyl-4-fluorobenzene-1,2-diamine (759 mg, 3.10 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (644 mg, 3.41 mmol), HOAt (464 mg, 3.41 mmol) and N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (654 mg, 3.41 mmol) in DCM (20 mL) was stirred at 0° C. for 1 h. The reaction mixture was then partitioned between DCM and a saturated solution of NaHCO3. The organic fraction was dried and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-50% EtOAc in cyclohexane) to afford the title compound (1.05 g, 81%) as a pale beige solid. LCMS (Method C): RT 3.66 min [M+H]+ 416.05

後処理

  1. customThe reaction mixture was then partitioned between DCM
  2. customThe organic fraction was dried
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-50% EtOAc in cyclohexane)

出典と根拠

ORDレコード
ord-78ae5010312d45bd813dcf735c14ec4a
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08653089B2

反応ノート

読み込み中…

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