Water → HCID 178490375, compound

HRID 1881063Notes

Reaction equation

HRID 1881063 reaction equation
O.[OH:2]OS([O-])=O.[K+].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]([C@H:34]2[CH2:39][CH2:38][C@H:37]([CH3:40])[CH2:36][CH2:35]2)[C:19](=[O:33])[NH:20][C:21]2[S:22][C:23]([S:26][C:27](C)(C)[C:28]([OH:30])=[O:29])=[CH:24][N:25]=2)=[CH:12][CH:11]=1>C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]([C@H:34]2[CH2:39][CH2:38][C@H:37]([CH3:40])[CH2:36][CH2:35]2)[C:19](=[O:33])[NH:20][C:21]2[S:22][C:23]([S:26]([CH2:27][C:28]([OH:30])=[O:29])=[O:2])=[CH:24][N:25]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 178490372HCID 178490372, compound

Product 1

HCID 178490375HCID 178490375, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To Montmorinonite (415 mg) was added H2O (98 μL) the mixture was stirred for 10 min before DCM (0.5 mL), oxone (428 mg, 0.70 mmol) and 2-{2-[3-[2-(4-methoxy-phenyl) -ethyl]-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-2-methyl-propionic acid (129 mg, 0.278 mmol) suspended in DCM (2.6 mL) was added in seqence. The mixture was stirred at rt for 1.5 hs. LCMS showed a 1:1 mixture of the sulfoxide and sulfone. The reaction mixture was filtered, washed with DCM and the filtrate was concentrated in vacuo. The mixture was purified by HPLC to give37 mg of {2-[3-[2-(4-methoxy-phenyl)-ethyl]-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazole-5-sulfinyl}-acetic acid.

Workup

  1. additionwas added in seqence
  2. filtrationThe reaction mixture was filtered
  3. washwashed with DCM
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe mixture was purified by HPLC to give37 mg of {2-[3-[2-(4-methoxy-phenyl)-ethyl]-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazole-5-sulfinyl}-acetic acid

Sources & evidence

ORD record
ord-364032971be34da081ad0812da5c6279
Source dataset
uspto-grants-2012_11
Patent number
US08318778B2

Reaction notes

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