Diethyl Ether → HCID 86596154, compound

HRID 2222938Notes

Reaction equation

HRID 2222938 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]2[C:25](=[O:30])[NH:26][CH2:27][C:28]#[N:29])=[CH:13][C:12]=1[F:31])(C)(C)C.[CH3:33][S:34]([OH:37])(=[O:36])=[O:35].CCOCC>O1CCCC1>[S:34]([OH:37])(=[O:36])(=[O:35])[CH3:33].[C:28]([CH2:27][NH:26][C:25]([CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH:19]1[CH2:18][S:17][C:14]1[CH:15]=[CH:16][C:11]([S:10][CH2:9][CH2:8][NH2:7])=[C:12]([F:31])[CH:13]=1)=[O:30])#[N:29]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 86596156HCID 86596156, compound

Product 1

HCID 86596154HCID 86596154, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-{4-[2-(Cyanomethylcarbamoyl)-cyclohexylmethylsulfanyl]-2-fluorophenylsulfanyl}-ethyl)-carbamic acid tert-butyl ester was dissolved in tetrahydrofuran (3 mL) and methanesulfonic acid (0.428 g, 6.6 mmol) was added. The reaction mixture was stirred at room temperature overnight, whereupon ether (100 mL) was added. The supernatant was discarded. The residue was triturated three times with ether (50 mL) then 10% tetrahydrofuran/ether, resulting in a white solid, N-cyanomethyl 2-[4-(2-aminoethylsulfanyl)-3-fluoro-phenylsulfanylmethyl]-cyclohexanecarboxamide mesylate, which was isolated by filtration in near quantitative mass recovery, with a small amount of t-butyl amide present as an inseparable impurity, resulting from addition of tert-butanol across the nitrile group under the acidic Boc-cleavage conditions. MS [ESI, (M+H)+] m/z=412 amu.

Workup

  1. additionwas added
  2. customThe residue was triturated three times with ether (50 mL)

Sources & evidence

ORD record
ord-67a01d810bde454e8514539cbbb1d672
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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