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Diisopropylethylamine → 2-[4-({[2-[(Tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]ethyl ethyl methylphosphonate

HRID 1013522
ノート
印刷プレビュー

反応式

HRID 1013522 の反応式
OC[C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[CH:15]=[CH:14][C:13]=2[NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:10])=[CH:5][CH:4]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH2:58]([O:60][P:61]([O:64][CH2:65][CH2:66]C1C=CC(C(O)=O)=CC=1)([CH3:63])=[O:62])[CH3:59].CCN(C(C)C)C(C)C>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH3:63][P:61](=[O:62])([O:64][CH2:65][CH3:66])[O:60][CH2:58][CH2:59][C:3]1[CH:4]=[CH:5][C:6]([C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[CH:15]=[CH:14][C:13]=2[NH:23][C:24]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:30])=[O:10])=[CH:7][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57607813Tert-butyl 2-{[4-(hydroxymethyl)benzoyl]amino}-4-thien-2-ylphenylcarbamateHCID 579259664-(2-{[Ethoxy(methyl)phosphoryl]oxy}ethyl)benzoic acid

生成物 1

HCID 57925964
2-[4-({[2-[(Tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]ethyl ethyl methylphosphonate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

1,1-dimethylethyl [2-({[4-(hydroxymethyl)phenyl]carbonyl}amino)-4-(2-thienyl)phenyl]carbamate (140 mg, 0.50 mmol), BOP (440 mg, 0.99 mmol), 4-(2-{[ethoxy(methyl)phosphoryl]oxy}ethyl)benzoic acid (90 mg, 0.33 mmol), and DIPEA (0.17 mL, 0.99 mmol) were stirred in DMF (1.1 mL) at 60° C. for 72 hours. The mixture was then diluted with saturated NaHCO3 solution and extracted with EtOAc. The organic layers were then washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification of the crude reaction mixture by MPLC (0-10% MeOH/DCM) resulted in the title compound as a yellow foam. MS cal'd 445 (MH+-Boc), exp 445 (MH+-Boc).

後処理

  1. extractionextracted with EtOAc
  2. washThe organic layers were then washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude
  6. customreaction mixture by MPLC (0-10% MeOH/DCM)

出典と根拠

ORDレコード
ord-8087cdb1fc6e43bea7b6e8bba7d9b57a
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07981874B2

反応ノート

読み込み中…

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