Sodium Carbonate → HCID 178523389, compound

HRID 245738Notes

Reaction equation

HRID 245738 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[CH2:16]([O:15][C:13]([NH:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]1)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 178511262HCID 178511262, compound

Product 1

HCID 178523389HCID 178523389, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To (trans)-4-(aminomethyl)cyclohexanecarboxylic acid (10 g, 44.5 mmol) in 1,4-dioxane (75 ml) and water (75 ml) was added dropwise benzyl chloroformate (6.99 ml, 49.0 mmol). The pH was kept between 7 and 8 by adding saturated aqueous sodium carbonate. After stirring for two hours the reaction mixture was concentrated in vacuo till half volume, 1M sodium hydroxide (aq) was added till pH=9 and the mixture was extracted with diethylether. 2M Hydrochloric acid was added till pH=1 was the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to yield (trans)-4-((benzyloxycarbonylamino)methyl)cyclohexanecarboxylic acid (12.03 g)

Workup

  1. concentrationwas concentrated in vacuo till half volume, 1M sodium hydroxide (aq)
  2. additionwas added till pH=9
  3. extractionthe mixture was extracted with diethylether
  4. addition2M Hydrochloric acid was added till pH=1
  5. extractionwas extracted twice with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fc08595eeb8d4c54a77d1ff7c21f416c
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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