Hydrochloric Acid → (-)-Asparagine

HRID 595609Notes

Reaction equation

HRID 595609 reaction equation
Cl.C[O:3][C:4](=[O:11])[C@H:5]([CH2:7][C:8](=[O:10])[NH2:9])[NH2:6].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-].Cl>CS(C)=O>[NH2:6][C@H:5]([C:4]([OH:11])=[O:3])[CH2:7][C:8](=[O:10])[NH2:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 6453494Methyl L-asparaginate monohydrochloride

Product 1

HCID 6267(-)-Asparagine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

HA-Asn was synthesized as follows. L-asparagine methyl ester hydrochloride (Bachem) was added to an anhydrous DMSO solution (5 mg/mL) of HA-TBA synthesized using HA-Na (99 kDa) as a starting material in Example 1-2 in an amount of 5 molar equivalents relative to the HA unit. Next, DMT-MM was added in an amount of 3-6 molar equivalents relative to the HA unit, and stirring was performed at room temperature overnight. After the reaction solution was reprecipitated with diethyl ether and the precipitate was dissolved in ultrapure water, 5N NaOH solution was added to adjust the pH to at least 12.5, and stirring was performed for an hour to perform carboxy deprotection via ethyl ester hydrolysis. Thereafter, the mixture was neutralized with 5N HCl solution and further dialyzed for purification against an aqueous solution of 0.3 M NaCl, distilled water, and ultrapure water in this order, and then the dialyzate was freeze-dried to give HA-Asn as a white solid.

Workup

  1. customHA-Asn was synthesized
  2. customsynthesized
  3. customAfter the reaction solution was reprecipitated with diethyl ether
  4. dissolutionthe precipitate was dissolved in ultrapure water
  5. addition5N NaOH solution was added
  6. stirringstirring
  7. waitwas performed for an hour
  8. customdeprotection via ethyl ester hydrolysis
  9. customfurther dialyzed for purification against an aqueous solution of 0.3 M NaCl
  10. distillationdistilled water, and ultrapure water in this order
  11. customthe dialyzate was freeze-dried

Sources & evidence

ORD record
ord-b6b8b0e7c49c47ab950927f9c3e669a2
Source dataset
uspto-grants-2016_01
Patent number
US09243077B2

Reaction notes

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