HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Hydroxide → (2S)-2-[[4-[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid

HRID 1681705
Notes
Print preview

Reaction equation

HRID 1681705 reaction equation
C(O)(=O)CC[C@H](NC(C1C=CC(NCC2N=C3C(N=C(NC3=O)N)=NC=2)=CC=1)=O)C(O)=O.BrC(CBr)C=O.NC1N=C(N)C(N)=C(O)N=1.NC1C=CC(CN[C@H](C(O)=O)CCC(O)=O)=CC=1.[OH-].[Na+].C([O-])(=O)CC[C@H](NC(C1C=CC(NCC2N=C3C(N=C(NC3=O)N)=NC=2)=CC=1)=O)C(O)=O.[Na+].[CH2:102]1[NH:107][C:106]2[NH:108][C:109]([NH2:113])=[N:110][C:111](=[O:112])[C:105]=2[N:104]([CH:114]=[O:115])[CH:103]1[CH2:116][NH:117][C:118]1[CH:123]=[CH:122][C:121]([C:124]([NH:126][C@H:127]([C:133]([O-:135])=[O:134])[CH2:128][CH2:129][C:130]([O-:132])=[O:131])=[O:125])=[CH:120][CH:119]=1.[Ca+2]>O.C(O)=O.[Pt]=O.O1CCOCC1>[CH:122]1[C:121]([C:124]([NH:126][C@H:127]([C:133]([OH:135])=[O:134])[CH2:128][CH2:129][C:130]([OH:132])=[O:131])=[O:125])=[CH:120][CH:119]=[C:118]([NH:117][CH2:116][CH:103]2[N:104]([CH:114]=[O:115])[C:105]3[C:111]([N:110]=[C:109]([NH2:113])[NH:108][C:106]=3[NH:107][CH2:102]2)=[O:112])[CH:123]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

12

Reactant 7

HCID 14798Sodium HydroxideHCID 922162,3-DibromopropanalHCID 53968688p-Aminobenzylglutamic acidHCID 135398658Folic Acid2×HCID 136359212Sodium folateHCID 178508811HCID 178508811, compound
HCID 178508911
calcium (2S)-2-[[4-[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioate

Product 1

HCID 178508910(2S)-2-[[4-[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 284Formic AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Folic acid and its salts can be prepared by any convenient method, for example 2,3-dibromopropionaldehyde, dissolved in a water miscible organic solvent (alcohol, dioxane), is added to a solution of equal molecular quantities of 2,4,5-triamino-6-hydroxypyrimidine and p-aminobenzylglutamic acid, maintaining a pH of about 4 by the controlled addition of alkali as the reaction progresses. If sodium hydroxide is used as the alkali, sodium folate is obtained. To make calcium leucovorin, folic acid is, for example simultaneously hydrogenated and formulated in 90 to 100% formic acid under the influence of platinum oxide catalyst to yield leucovorin. Conversion to the calcium salt may be accomplished by dissolving the leucovorin in sodium hydroxide solution, treating the calcium chloride, and precipitating with ethanol.

Workup

  1. temperaturemaintaining a pH of about 4
  2. additionby the controlled addition of
  3. customalkali as the reaction progresses
  4. customis obtained

Sources & evidence

ORD record
ord-fe8b3ad1ad6d44d1a916cb6ae7124555
Source dataset
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05173488

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes