Citric Acid → HCID 178453971, compound

HRID 1896238Notes

Reaction equation

HRID 1896238 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.[C:11](=[O:14])([O-])[O-:12].[Na+].[Na+].C(O)(=O)[CH2:18][C:19]([CH2:24]C(O)=O)([C:21](O)=O)O>O1CCOCC1>[CH3:18][C:19]([CH3:24])([O:12][C:11]([NH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1)=[O:14])[CH3:21]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 10340Sodium CarbonateHCID 178511566HCID 178511566, compound

Product 1

HCID 178453971HCID 178453971, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Boc-anhydride (2.30 ml, 4.19 mmol) was added to a solution of cis-4-amino cyclohexyl carboxylic acid (1.00 g, 6.99 mmol) in aqueous solution of sodium carbonate (6 ml, 5% w/w) in dioxane (14 ml) at 0° C. The reaction mixture was allowed to warm up to room temperature and stirred for 18 h. The reaction mixture was acidified to pH˜4 using citric acid. The compound was extracted with ethyl acetate (3×30 ml) and washed with brine (15 ml). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated and dried to afford 1.2 g (71.8%) of cis-4-[[(1,1-dimethylethoxy)carbonyl]amino]-cyclohexanecarboxylic acid.

Workup

  1. extractionThe compound was extracted with ethyl acetate (3×30 ml)
  2. washwashed with brine (15 ml)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customdried

Sources & evidence

ORD record
ord-0a4a4c71855140a58b314a623a7c09d0
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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