Formic Acid → 10-Formylfolic acid

HRID 1084973Notes

Reaction equation

[C:1]([OH:32])(=[O:31])[CH2:2][CH2:3][C@H:4]([NH:8][C:9]([C:11]1[CH:30]=[CH:29][C:14]([NH:15][CH2:16][C:17]2[N:28]=[C:27]3[C:20]([N:21]=[C:22]([NH:24][C:25]3=[O:26])[NH2:23])=[N:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:10])[C:5]([OH:7])=[O:6].[CH:33](O)=[O:34]>>[CH:33]([N:15]([CH2:16][C:17]1[N:28]=[C:27]2[C:20]([N:21]=[C:22]([NH:24][C:25]2=[O:26])[NH2:23])=[N:19][CH:18]=1)[C:14]1[CH:13]=[CH:12][C:11]([C:9](=[O:10])[NH:8][C@H:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2][C:1]([OH:32])=[O:31])=[CH:30][CH:29]=1)=[O:34]

Participants

Reactant 2

HCID 284Formic Acid

HCID 135398658Folic Acid

Product 1

HCID 13540502310-Formylfolic acid

Procedure

5-CHO- and 5-Me-(6R,S)-THF can be prepared in a known manner from folic acid. Formylation with formic acid produces 10-formyl-folic acid (10-CHO-FA). The latter can subsequently be catalytically hydrogenated to 10-formyl-tetrahydrofolic acid (10-CHO-THF). 5,10-Methenyl-tetrahydrofolic acid (I; 5,10-CH-THF; "anhydroleucovorin") can be obtained from the latter by dehydration: ##STR1##

Sources & evidence

ORD record: ord-2e91b10d6fce4befbcfb94e2a460c79d
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05006655

Reaction notes

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