Pyridine → HCID 9870934, compound

HRID 1795062Notes

Reaction equation

HRID 1795062 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C@H:8]([NH:16]C(=O)OC(C)(C)C)[C:9](=[O:15])[N:10]2[CH2:14][CH2:13][S:12][CH2:11]2)[CH2:4][CH2:3]1.[CH:24]1[C:29]([S:30](Cl)(=[O:32])=[O:31])=[CH:28][CH:27]=[C:26]([I:34])[CH:25]=1.N1C=CC=CC=1>C(Cl)Cl>[NH2:16][C@@H:8]([CH:5]1[CH2:4][CH2:3][CH:2]([NH:1][S:30]([C:29]2[CH:24]=[CH:25][C:26]([I:34])=[CH:27][CH:28]=2)(=[O:32])=[O:31])[CH2:7][CH2:6]1)[C:9](=[O:15])[N:10]1[CH2:14][CH2:13][S:12][CH2:11]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73994-Iodobenzenesulfonyl chlorideHCID 178454230HCID 178454230, compound

Product 1

HCID 9870934HCID 9870934, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 50 mg (0.139 mmol) of tert-butyl trans-(1S)-1-(4-aminocyclohexyl)-2-oxo-2-(1,3-thiazolidin-3-yl)ethyl-carbamate in 1 mL of methylene chloride was added 53 mg (0.175 mmol) of pipsyl chloride, and 0.022 mL (0.27 mmol) of pyridine, and the reaction was stirred at ambient temperature for 16 h. The solvent was removed in vacuo and the product purified by preparative thin layer chromatography (TLC) (silica gel, 5:95 methanol:methylene chloride) afforded 51 mg of the title compound as is Boc carbamate. Deprotection was effected by treatment with 2 mL of a 1:1 mixture of trifluoroacetic acid:methylene chloride at ambient temperature for 2 h, followed by concentration in vacuo and removal of the excess trifluoroacetic acid by azeotropic distillation with methylene chloride. Purification by preparative TLC (silica gel, 9:1:90 methanol:concentrated ammonium hydroxide:methylene chloride) afforded 37 mg of the title compound. 1H NMR (400 MHz, CD3OD) δ 7.94 (d, 2H, J=8 Hz), 7.58 (d, 2H, J=8 Hz), 4.64–4.62 (m, 0.45H), 4.58–4.52 (m, 1H), 4.47–4.43 (m, 0.55H), 3.91–3.64 (m, 2H), 3.41 (d, 0.45H, J=7 Hz), 3.37 (d, 0.55H, J=7 Hz), 3.07 (t, 1.1H, J=6 Hz), 3.02 (t, 0.9H, J=6 Hz), 3.00–2.92 (m, 1H), 1.84–1.72 (m, 3H), 1.59–1.52 (m, 1H), 1.48–1.38 (m, 1H), 1.23–1.10 (m, 3H), 1.09–0.97 (m, 1H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe product purified by preparative thin layer chromatography (TLC) (silica gel, 5:95 methanol:methylene chloride)

Sources & evidence

ORD record
ord-7d11847679c74aedbaf371d954c91dec
Source dataset
uspto-grants-2006_04
Patent number
US07026316B2

Reaction notes

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