Hydrochloric Acid → HCID 68999551, compound

HRID 660672Notes

Reaction equation

HRID 660672 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[S:19](=[O:21])(=[O:20])[N:18]([CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:17](=[O:28])[CH2:16]2)=[C:11]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:10]=1.C(N(C(C)C)CC)(C)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48].Cl>C(Cl)Cl>[CH2:30]([O:29][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[N:15]1[CH2:16][C:17](=[O:28])[N:18]([CH2:22][CH2:23][Si:24]([CH3:26])([CH3:27])[CH3:25])[S:19]1(=[O:21])=[O:20])[CH2:8][C@@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]1[NH:1][S:47]([CH3:46])(=[O:49])=[O:48])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68839756HCID 68839756, compound

Product 1

HCID 68999551HCID 68999551, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[4-((1S*,2R*)-2-aminocyclohexylmethyl)-2-benzyloxy-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (153 mg, 0.238 mmol) and diisopropylethylamine (92 mg, 0.712 mmol) in methylene chloride (5 mL) is added methanesulfonyl chloride (30 mg, 0.258 mmol) and the mixture is stirred at RT for 14 h. The mixture is poured into 1N HCl and extracted with EtOAc and the organic phase is washed with saturated NaHCO3. The organic phase is dried over magnesium sulfate and the solvent removed under reduced pressure to give the title compound.

Workup

  1. extractionextracted with EtOAc
  2. washthe organic phase is washed with saturated NaHCO3
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6ccf9f0361b744f9b83ede209c4dcddc
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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