Hydrochloric Acid → HCID 15003916, compound

HRID 1590978Notes

Reaction equation

HRID 1590978 reaction equation
[NH2:1][C@H:2]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][C:4](=[O:6])[OH:5].[NH:12]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C@H:13]([C:24](ON1C(=O)CCC1=O)=[O:25])[C@@H:14]([CH3:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.Cl>C1COCC1.CN(C=O)C>[NH:12]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[C@H:13]([C:24]([NH:1][C@H:2]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][C:4](=[O:5])[OH:6])=[O:25])[C@@H:14]([CH3:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1074984-Ethyl hydrogen L-aspartateHCID 12879029Boc-Thr(Bzl)-OSu

Product 1

HCID 15003916HCID 15003916, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension consisting of 2.3 g of H-Asp-OEt, 5.8 g of Boc-Thr(Bzl)-OSu in 20 ml of THF and 20 ml of DMF, was added 2 ml of triethylamine under an ice-cooling condition and the mixture was stirred for 1 hour so as to the pH of the reaction mixture was adjusting to about pH 7, and the reaction was continued for 36 hours. The reaction mixture was concentrated under reduced pressure and the residue thus obtained was acidified by adding 1N-hydrochloric acid, and extracted with ethyl acetate (80 ml×3 times). The organic layer was washed with water, then with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, The ethyl acetate extract was concentrated under reduced pressure and the residue thus obtained was crystallized and recrystallized from diethyl ether-petroleum ether. 5.59 Grams (yield: 86.6%) of the above-mentioned objective product was obtained.

Workup

  1. temperaturecooling condition
  2. waitthe reaction was continued for 36 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue thus obtained
  5. extractionextracted with ethyl acetate (80 ml×3 times)
  6. washThe organic layer was washed with water
  7. dry with materialwith a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate
  8. extractionThe ethyl acetate extract
  9. concentrationwas concentrated under reduced pressure
  10. customthe residue thus obtained
  11. customwas crystallized
  12. customrecrystallized from diethyl ether-petroleum ether

Sources & evidence

ORD record
ord-8d08a1618c5a407e91c38cd41ab09b8c
Source dataset
uspto-grants-1993_04
Patent number
US05204326

Reaction notes

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