Citric Acid → HCID 71268183, compound

HRID 1519721Notes

Reaction equation

HRID 1519721 reaction equation
[OH-].[K+].C1COCC1.C([O:10][C:11](=[O:43])[C@:12]([N:18]([CH3:42])[C:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)=[O:20])([CH3:17])[C:13]([NH:15][CH3:16])=[O:14])C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:11]([C@:12]([N:18]([CH3:42])[C:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)=[O:20])([CH3:17])[C:13]([NH:15][CH3:16])=[O:14])([OH:43])=[O:10]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 71268178HCID 71268178, compound

Product 1

HCID 71268183HCID 71268183, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution (2.0 mL) of potassium hydroxide (0.11 g) was added to a THF (2.0 mL)-methanol (2.0 mL) solution of 4-{2-[(4′-{[(2S)-1-ethoxy-2-methyl-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl-4-yl)oxy]ethyl}morpholine (93 mg) as obtained in Example 19-(3), and the mixture was stirred for 16 hours at room temperature. The reaction mixture was adjusted to pH 6 with a 10% aqueous solution of citric acid, and extracted with chloroform. The organic layer was separated using a phase separator, and the solvent was distilled off under reduced pressure to obtain 4-{2-[(4′-{[(2S)-2-carboxy-1-(methylamino)-1-oxopropan-2-yl](methyl)carbamoyl}biphenyl-4-yl)oxy]ethyl}morpholine (light brown oil) (58 mg, 65%).

Workup

  1. customas obtained in Example 19-(3)
  2. extractionextracted with chloroform
  3. customThe organic layer was separated
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-93ae9d1a466b4e7288548fc5bc2c41e1
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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