Hydrochloric Acid → HCID 54329500, compound

HRID 369782Notes

Reaction equation

HRID 369782 reaction equation
C[O:2][C:3]([C:5]1[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=1[CH2:7][C@@H:8]([C:10]([O-:12])=[O:11])[NH2:9])=[O:4].O[Li].O.C(O)(C(F)(F)F)=O.Cl>CC#N.O.C1COCC1>[C:3]([C:5]1[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=1[CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])([OH:4])=[O:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 168937Lithium hydroxide, monohydrateHCID 86755970HCID 86755970, compound

Product 1

HCID 54329500HCID 54329500, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 50 mL 3-necked flask equipped with a magnetic stirrer and a nitrogen inlet were added 0.12 g of methyl N-(4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-5-O-methyl-L-glutam-1-yl)-2-(methoxycarbonyl)-L-phenylalaninate and 10 mL of 1:1 H2O:THF. The mixture was treated with 29 mg of LiOH.H2O (J. T. Baker Chemical Co., Phillipsburg, N.J.) and stirred at RT under nitrogen. After 48 h, analysis by HPLC (C18, 75:25:0.1 H2O:MeCN:TFA) indicated a major new component at k'=1.70 (ca. 90%) and three minor components at K'=0.60, 1.03, and 2.58. The solution was neutralized by dropwise addition of 1 N aqueous HCl and concentrated in vacuo to dryness. The residue was dissolved in 10 mL of MeOH was removed by rotary evaporation and the remaining suspension was frozen and lyophilized to afford 65 mg (45%) of N-(4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-L-glutam-1-yl)-2-carboxy-L-phenylalanine as a yellow powder, m.p. 160° C. (dec).

Workup

  1. customTo a 50 mL 3-necked flask equipped with a magnetic stirrer and a nitrogen inlet
  2. concentrationconcentrated in vacuo to dryness
  3. dissolutionThe residue was dissolved in 10 mL of MeOH
  4. customwas removed by rotary evaporation
  5. temperaturethe remaining suspension was frozen

Sources & evidence

ORD record
ord-86d8eb8d77e4452db9915ecd599f113d
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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