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 1433082Notes

Reaction equation

HRID 1433082 reaction equation
[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]

Participants

4

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

{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)+.

Workup

  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

Sources & evidence

ORD record
ord-0407b79457774f7fbaf5ea9a87b7b84a
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

Loading…