Citric Acid → HCID 86747321, compound

HRID 1656734Notes

Reaction equation

HRID 1656734 reaction equation
[N+](C1C=CC([O:10][C:11](=O)[CH2:12][NH:13][C:14](=[O:27])[C@H:15]([CH:24]([CH3:26])[CH3:25])[NH:16]C(OC(C)(C)C)=O)=CC=1)([O-])=O.C(N(CC)CC)C.[NH2:36][C@H:37]1[C@@H:41]([CH3:42])[CH2:40][N:39]([C:43]2[C:52]([F:53])=[CH:51][C:50]3[C:54](=[O:60])[C:55]([C:57]([OH:59])=[O:58])=[CH:56][N:48]4[C:49]=3[C:44]=2[CH2:45][CH2:46][N:47]4[CH3:61])[CH2:38]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(Cl)[Cl:76]>O>[ClH:76].[NH2:16][CH:15]([CH:24]([CH3:26])[CH3:25])[C:14]([NH:13][CH2:12][C:11]([NH:36][C@H:37]1[C@@H:41]([CH3:42])[CH2:40][N:39]([C:43]2[C:52]([F:53])=[CH:51][C:50]3[C:54](=[O:60])[C:55]([C:57]([OH:59])=[O:58])=[CH:56][N:48]4[C:49]=3[C:44]=2[CH2:45][CH2:46][N:47]4[CH3:61])[CH2:38]1)=[O:10])=[O:27]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 6344DichloromethaneHCID 8471TriethylamineHCID 9928823HCID 9928823, compoundHCID 53688065HCID 53688065, compound

Product 1

HCID 86747321HCID 86747321, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

758 mg (2 mmol) of (N-t-butoxycarbonylvalyl)glycine p-nitrophenyl ester, 202 mg (2 mmol) of triethylamine and 716 mg (2 mmol) of the compound (30) obtained in Example 5 (1) were added to 10 ml of methylene chloride. The mixture solution was stirred overnight at room temperature. 10 ml of water was added to the solution and the solution was acidified with citric acid. The organic layer was separated and was removed by distillation after drying over sodium sulfate. Ethyl acetate--ether was added to the residue, the product came out of the solution, and the solid was filtered off. The solid was added to 10 mi of methanol, and 2.5 ml of 4N hydrochloride solution in dioxane was added to the solution. After the solution was stirred at room temperature for 30 minutes, the solvent was removed by distillation. The powder was filtered off and washed successively with ethanol and ether to obtain 618 mg of the subject compound (96) in a 58% yield. The results of the analysis of this compound were as follows:

Workup

  1. customThe organic layer was separated
  2. customwas removed by distillation
  3. dry with materialafter drying over sodium sulfate
  4. additionEthyl acetate--ether was added to the residue
  5. filtrationthe solid was filtered off
  6. additionThe solid was added to 10 mi of methanol, and 2.5 ml of 4N hydrochloride solution in dioxane
  7. additionwas added to the solution
  8. stirringAfter the solution was stirred at room temperature for 30 minutes
  9. customthe solvent was removed by distillation
  10. filtrationThe powder was filtered off
  11. washwashed successively with ethanol and ether

Sources & evidence

ORD record
ord-8cd280d65b3141a99712a431dbe57540
Source dataset
uspto-grants-1993_10
Patent number
US05254685

Reaction notes

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