Citric Acid → HCID 44544416, compound

HRID 1254626Notes

Reaction equation

HRID 1254626 reaction equation
[CH2:1]([NH:8][C:9]([N:11]1[CH:16]2[C@H:17]([CH3:41])[N:18]([CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[C:35]4[C:40]=3[N:39]=[CH:38][CH:37]=[CH:36]4)[C:19](=[O:29])[C@H:20]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[N:15]2[C:14](=[O:42])[CH2:13][N:12]1[CH3:43])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:44](Cl)(Cl)(Cl)=[O:45].[OH2:49].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:53]>O1CCCC1>[P:44]([OH:45])([OH:53])([O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C@@H:20]2[N:15]3[CH:16]([N:11]([C:9](=[O:10])[NH:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[N:12]([CH3:43])[CH2:13][C:14]3=[O:42])[C@H:17]([CH3:41])[N:18]([CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[C:35]4[C:40]=3[N:39]=[CH:38][CH:37]=[CH:36]4)[C:19]2=[O:29])=[CH:27][CH:26]=1)=[O:49]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 24813Phosphorus oxychlorideHCID 44544414HCID 44544414, compound2×

Product 1

HCID 44544416HCID 44544416, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of (6S,9S)—N-benzyl-6-(4-hydroxybenzyl)-2,9-dimethyl-4,7-dioxo-8-(quinolin-8-ylmethyl)octahydro-1H-pyrazino[2,1-c][1,2,4]triazine-1-carboxamide (Compound 1-5) 325 mg (0.43 mmol) and TEA 179 μl (1.29 mmol) in tetrahydrofuran 6 ml, phosphoryl chloride 200 μl (2.15 mmol) was added at 0° C. and stirred at room temperature for 4 hours. Water was added to the reaction mixture and stirred additional overnight. The reaction mixture was acidified with 10%-citric acid 30 ml and extracted with chloroform 150 ml. The organic phase was dried with magnesium sulfate and filtered. The filtrate was concentrated in vacuo to obtain the title compound 179 mg (60%).

Workup

  1. stirringstirred additional overnight
  2. extractionextracted with chloroform 150 ml
  3. dry with materialThe organic phase was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f0cfe7bcc7f34e8f86265cad456ce8ad
Source dataset
uspto-grants-2013_06
Patent number
US08455488B2

Reaction notes

Loading…