Hydrochloric Acid → HCID 67908467, compound

HRID 1981237Notes

Reaction equation

HRID 1981237 reaction equation
C([O:8][C:9](=[O:27])[C@H:10]([NH:15][C@H:16]1[C@H:24]2[C@H:19]([C@@H:20]3C[C@H:23]2[CH:22]=[CH:21]3)C(=O)O1)[CH2:11][CH:12]([CH3:14])[CH3:13])C1C=CC=CC=1.[ClH:28]>O>[ClH:28].[CH2:16]([NH:15][C@@H:10]([C:9]([OH:27])=[O:8])[CH2:11][CH:12]([CH3:14])[CH3:13])[C:24]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10981484HCID 10981484, compound

Product 1

HCID 67908467HCID 67908467, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

A mixture of 2 g of the product of Example 1, 15 ml of demineralized water and 1.5 ml of hydrochloric acid was stirred at 20° C. for one hour and was then heated at 60° C. for one hour and then cooled to 20° C. 15 ml of water were added to the mixture and the mixture was extracted with methylene chloride. The organic phase was washed with aqueous N sodium hydroxide solution and then with water until the wash water was neutral, dried and evaporated to dryness under reduced pressure. The residue was taken up in 10 ml of ether and a current of hydrogen chloride was slowly bubbled through the solution. The mixture was vacuum filtered to obtain 800 mg of benzyl D-leucine hydrochloride melting at 137° C. and having a specific rotation of [α]D20 =+3.5° (c=1% in 0.1 N hydrochloric acid).

Workup

  1. temperaturewas then heated at 60° C. for one hour
  2. temperaturecooled to 20° C
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe organic phase was washed with aqueous N sodium hydroxide solution
  5. customdried
  6. customevaporated to dryness under reduced pressure
  7. customa current of hydrogen chloride was slowly bubbled through the solution
  8. filtrationfiltered

Sources & evidence

ORD record
ord-caab30d7744045f8a469547c40cfa89c
Source dataset
uspto-grants-1985_04
Patent number
US04513139

Reaction notes

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