Hydrochloric Acid → HCID 178501226, compound

HRID 2118250Notes

Reaction equation

HRID 2118250 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][CH2:6]1)=[O:4].[CH3:19]I.[H-].[Na+].Cl>CN(C=O)C.CCOCC>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH3:19])[CH2:9][CH2:10]1)=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178501239HCID 178501239, compound

Product 1

HCID 178501226HCID 178501226, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

16.2 g (62.95 mmol) of trans-4-tert-butoxy carbonylamino-cyclohexanecarboxylic acid methyl ester and 5.87 mL (94.43 mmol, 1.5 eq) of methyl iodide in 100 ml DMF were treated under stirring and ice-cooling with 3.57 g (81.84 mmol, 1.3 eq) of NaH (55% in oil). The solution was stirred at RT for 20 h and then treated under ice-cooling with 1M HCl. The reaction mixture was dissolved in ether and washed 4 times with water. The ether-phases were concentrated under reduced pressure to yield 17.5 g (quantitative) of trans-4-(tert-butoxycarbonyl-methyl-amino)-cyclohexanecarboxylic acid methyl ester, MS: 201 (M−OC4H9).

Workup

  1. stirringThe solution was stirred at RT for 20 h
  2. additiontreated under ice-
  3. washwashed 4 times with water
  4. concentrationThe ether-phases were concentrated under reduced pressure

Sources & evidence

ORD record
ord-8a1dd650dcd4459fb1531a7a6ff0d24e
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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