Water → HCID 178474847, compound

HRID 78866Notes

Reaction equation

HRID 78866 reaction equation
[CH2:1]1[CH2:6][C@H:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3][C@H:2]1[CH2:10][NH2:11].S(=O)(=O)(O)O.O.[C:18](OC(=O)C)(=[O:20])[CH3:19]>>[C:18]([NH:11][CH2:10][C@H:2]1[CH2:3][CH2:4][C@H:5]([C:7]([OH:9])=[O:8])[CH2:6][CH2:1]1)(=[O:20])[CH3:19]

Participants

5

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 7918Acetic Anhydride2×HCID 178511262HCID 178511262, compound

Product 1

HCID 178474847HCID 178474847, compoundYield 98%

Procedure

Tranexamic acid (10 g, 63.6 mmol) was suspended in acetic anhydride (50 mL), this suspension was added with concentrated sulfuric acid (0.01 mL) at room temperature, and the mixture was stirred overnight at the same temperature. Under ice cooling, the reaction mixture was added with water (100 mL), and the mixture was stirred at room temperature for 1 hour to decompose excess acetic anhydride. The reaction solution was concentrated under reduced pressure, and the residue was further azeotroped with toluene. The resulting precipitates were collected by filtration, washed with ether, and dried under reduced pressure to obtain trans-{4-[(acetylamino) methyl]cyclohexyl}carboxylic acid as white solid (12.46 g, 98%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe residue was further azeotroped with toluene
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed with ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-5d7da78f6af24895a4bdf78f795ba0fe
Source dataset
uspto-grants-2014_09
Patent number
US08841478B2

Reaction notes

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