Hydrochloric Acid → HCID 178508844, compound

HRID 2288554Notes

Reaction equation

HRID 2288554 reaction equation
[NH2:1][C:2]1[NH:7][C:6]2[NH:8][CH:9]=[C:10]([CH2:11][CH2:12][C:13]3[CH:30]=[CH:29][C:16]([C:17]([NH:19][C@H:20]([C:26]([OH:28])=[O:27])[CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:18])=[CH:15][CH:14]=3)[C:5]=2[C:4](=[O:31])[N:3]=1.Cl.[OH-].[Na+:34]>O>[Na+:34].[Na+:34].[NH2:1][C:2]1[NH:7][C:6]2[NH:8][CH:9]=[C:10]([CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][C:16]([C:17]([NH:19][C@H:20]([C:26]([O-:28])=[O:27])[CH2:21][CH2:22][C:23]([O-:25])=[O:24])=[O:18])=[CH:29][CH:30]=3)[C:5]=2[C:4](=[O:31])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 178508842(2S)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid

Product 1

HCID 178508844HCID 178508844, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid from Example 7 was dissolved in 3.8 mL of water and 2.2 ml of 1N sodium hydroxide. The pH of the mixture was adjusted to 7.5-8.5 using dilute hydrochloric acid and 1N sodium hydroxide. The solution was heated to 70° C. and 40 mL of 3A alcohol were added. The solution was allowed to cool to room temperature during which time a thick slurry developed. The solids were filtered and washed with 4:1 ethanol:water. The solids were dried at 50° C. in a vacuum oven. 640 milligrams of the title compound were recovered as a solid.

Workup

  1. temperatureto cool to room temperature during which time a thick slurry
  2. filtrationThe solids were filtered
  3. washwashed with 4:1 ethanol
  4. customThe solids were dried at 50° C. in a vacuum oven
  5. custom640 milligrams of the title compound were recovered as a solid

Sources & evidence

ORD record
ord-1b5b31186a0247d483e866bd8fd75ddf
Source dataset
uspto-grants-2000_07
Patent number
US06090168

Reaction notes

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