Diethyl Ether → HCID 86760668, compound

HRID 2222934Notes

Reaction equation

HRID 2222934 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23][CH2:24][CH2:25][NH:26]C(OC(C)(C)C)=O)=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:6])#[N:2].[CH3:34][S:35]([OH:38])(=[O:37])=[O:36].CCOCC>O1CCCC1>[S:35]([OH:38])(=[O:37])(=[O:36])[CH3:34].[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23][CH2:24][CH2:25][NH2:26])=[CH:19][CH:18]=1)(=[O:15])=[O:16])=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 86760667HCID 86760667, compound

Product 1

HCID 86760668HCID 86760668, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-N-cyanomethyl-2-[4-(tert-butoxycarbonylaminoethylsulfanyl)-benzenesulfonylmethyl]cyclohexanecarboxamide (0.35 g, 0.706 mmol) in tetrahydrofuran (2 mL) at room temperature was added dry methanesulfonic acid (0.183 mL, 2.82 mmol). The reaction mixture was stirred overnight at room temperature. Ether (200 mL) was added. The supernatant was decanted. The residue was triturated twice with ether (50 mL each) and was then precipitated from methanol/ether, giving the title compound as its mesylate salt. MS [ESI, (M−H)−] m/z=394 amu.

Workup

  1. customThe supernatant was decanted
  2. customThe residue was triturated twice with ether (50 mL each)
  3. customwas then precipitated from methanol/ether

Sources & evidence

ORD record
ord-d425e271ad7c421cbb4600c8c7935357
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

Loading…