Citric Acid → HCID 131713883, compound

HRID 1632430Notes

Reaction equation

HRID 1632430 reaction equation
[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][C:4](=[O:6])[NH2:5].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:35][C@H:36]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:37][CH:38]([CH3:40])[CH3:39].Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C(N(CC)CC)C.CN(C)C=O>[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7]([NH:35][C@H:36]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:37][CH:38]([CH3:40])[CH3:39])=[O:9])[CH2:3][C:4](=[O:6])[NH2:5]

Participants

9

Reactant 5

HCID 311Citric AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 75314Benzyloxycarbonyl-asparagineHCID 11658447L-Leucine, ethyl ester, hydrochloride (1:1)

Product 1

HCID 131713883HCID 131713883, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

5.32 Grams of Z-Asn-OH was dissolved in 60 ml of tetrahydrofuran, 10 ml of dimethylformamide and 2.04 ml of N-methylmorpholine, to this mixture was added 40 ml of a dimethylformamide solution containing 2.64 ml of isobutyl chloroformate, 3.91 g of H-Leu-OEt.HCl and 2.80 ml of triethylamine and the reaction was carried out by a procedure similar to that described in Reference example 2. After removal of the solvent by distillation, to the residue obtained was added 1M-citric acid, the precipitate formed was collected by filtration, washed with water, dried under a reduced pressure, then was recrystallized from ethyl acetate to obtain 6.1 g of Z-Asn-Leu-OEt.

Workup

  1. customAfter removal of the solvent
  2. distillationby distillation
  3. customto the residue obtained
  4. customthe precipitate formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried under a reduced pressure
  8. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5c08abaeb9b14328a782606ae4758d9a
Source dataset
uspto-grants-1984_10
Patent number
US04474754

Reaction notes

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