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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
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HRID 1433082 반응식
[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]
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반응물 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

생성물 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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

{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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-0407b79457774f7fbaf5ea9a87b7b84a
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612075B2

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