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Acetic Acid Mixture with Hydrobromic Acid → {5-Aminomethyl-2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl}-acetic acid ethyl ester

HRID 1433082
ノート
印刷プレビュー

反応式

HRID 1433082 の反応式
[CH2:1]([O:3][C:4](=[O:44])[CH2:5][C:6]1[N:7]=[C:8]([CH2:23][N:24]2[CH2:29][CH2:28][N:27]([S:30]([C:33]3[S:37][C:36]4[CH:38]=[C:39]([Cl:42])[CH:40]=[CH:41][C:35]=4[CH:34]=3)(=[O:32])=[O:31])[CH2:26][C:25]2=[O:43])[S:9][C:10]=1[CH2:11][NH:12]C(OCC1C=CC=CC=1)=O)[CH3:2].Br.CC(O)=O>CCOCC>[CH2:1]([O:3][C:4](=[O:44])[CH2:5][C:6]1[N:7]=[C:8]([CH2:23][N:24]2[CH2:29][CH2:28][N:27]([S:30]([C:33]3[S:37][C:36]4[CH:38]=[C:39]([Cl:42])[CH:40]=[CH:41][C:35]=4[CH:34]=3)(=[O:32])=[O:31])[CH2:26][C:25]2=[O:43])[S:9][C:10]=1[CH2:11][NH2:12])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 69026982{5-(Benzyloxycarbonylamino-methyl)-2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl}-acetic acid ethyl ester

生成物 1

HCID 69024621{5-Aminomethyl-2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl}-acetic acid ethyl ester

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

{5-(Benzyloxycarbonylamino-methyl)-2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl}-acetic acid ethyl ester (40 mg, 0.06 mmol) is treated with 30% HBr/HOAc (1 mL) for 7 h. Ether (10 mL) is added and the resulting precipitate is washed twice with ether. The resulting salt is partitioned between EtOAc (15 mL) and NaHCO3 solution (10 mL). The organic phase is washed with NaHCO3 and brine (2×10 mL), dried (MgSO4) and concentrated to provide {5-aminomethyl-2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl}-acetic acid ethyl ester. 1H NMR (300 MHz, DMSO) δ 8.32 (d, 1H), 8.17 (s, 1H), 8.08-8.02 (m, 2H), 7.57 (dd, 1H), 4.62 (s, 2H), 4.02 (q, 2H), 3.81 (s, 2H), 3.74 (s, 2H), 3.64 (s, 2H), 3.48-3.35 (m, 4H), 2.48 (t, 3H); MS (ion spray) 543 (M+H)+.

後処理

  1. washthe resulting precipitate is washed twice with ether
  2. customThe resulting salt is partitioned between EtOAc (15 mL) and NaHCO3 solution (10 mL)
  3. washThe organic phase is washed with NaHCO3 and brine (2×10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-0407b79457774f7fbaf5ea9a87b7b84a
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07612075B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート