Sulfuric Acid → 1-Amino-4-benzyloxycyclohexane-1-carboxylic acid

HRID 2393938Notes

Reaction equation

HRID 2393938 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])NC1=O.[CH2:8]([O:15][CH:16]1[CH2:21][CH2:20]C(=O)[CH2:18][CH2:17]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.S(=O)(=O)(O)[OH:24]>[OH-].[Ba+2].[OH-]>[NH2:1][C:7]1([C:5]([OH:6])=[O:24])[CH2:18][CH2:17][CH:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 702323244-Benzyloxycyclohexanone hydantoin

Product 1

HCID 189701811-Amino-4-benzyloxycyclohexane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6093286Barium hydroxideSolvent

Procedure

The hydantoin 42 is hydrolyzed by refluxing with 10 mL of a barium hydroxide solution (saturated at room temperature) for 16 h (Step 39). The solution is neutralized to pH 6 with 2N sulfuric acid and evaporated to dryness in vacuo. The residue is extracted with 50 mL of hot methanol, filtered, and washed with 50 mL of hot methanol. The methanol solutions are combined and evaporated.

Workup

  1. customevaporated to dryness in vacuo
  2. extractionThe residue is extracted with 50 mL of hot methanol
  3. filtrationfiltered
  4. washwashed with 50 mL of hot methanol
  5. customevaporated

Sources & evidence

ORD record
ord-c565e889673b4d62a19824ce5f2cccc0
Source dataset
uspto-grants-1998_09
Patent number
US05808146

Reaction notes

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