Dimethylamine, hydrochloride → HCID 58084197, compound

HRID 905973Notes

Reaction equation

HRID 905973 reaction equation
C[CH2:2][N:3](C(C)C)[CH:4](C)C.[C:10]([O:14][C:15]([NH:17][C@H:18]1[CH2:23][CH2:22][CH2:21][C@H:20]([C:24]([OH:26])=O)[CH2:19]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].Cl.CNC.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:10]([O:14][C:15](=[O:16])[NH:17][C@H:18]1[CH2:23][CH2:22][CH2:21][C@H:20]([C:24](=[O:26])[N:3]([CH3:4])[CH3:2])[CH2:19]1)([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 51386890(1S,3S)-3-{[(tert-butoxy)carbonyl]amino}cyclohexane-1-carboxylic acid

Product 1

HCID 58084197HCID 58084197, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (1.8 mL, 10.3 mmol) was added at RT to a mixture of racemic trans 3-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (1.00 g, 4.109 mmol), dimethylamine hydrochloride (0.0.503 g, 6.17 mmol), and EDCI (1.182 g, 6.17 mmol) in 13 mL of DCM. The resulting mixture was stirred at RT for 16 hours before being partitioned between H2O and DCM. The aqueous layer was back extracted twice with DCM. The combined organic layers were dried (Na2SO4), filtered, and evaporated. The residue was purified by SiO2 flash chromatography (DCM/MeOH 0 to 5% MeOH) to give 0.438 g (39%) of racemic trans 3-dimethylcarbamoyl-cyclohexyl carbamic acid tert-butyl ester.

Workup

  1. custombefore being partitioned between H2O and DCM
  2. extractionThe aqueous layer was back extracted twice with DCM
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by SiO2 flash chromatography (DCM/MeOH 0 to 5% MeOH)

Sources & evidence

ORD record
ord-533ff8016fa14208af2fb145c9f8183c
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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