Hydrochloric Acid → 6R-Tetrahydrofolic acid

HRID 650222Notes

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

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 135444742Tetrahydrofolic acid

Product 1

HCID 1354158766R-Tetrahydrofolic acid

Procedure

One half of the mother liquor is precipitated with 1.1 g of ethanol, giving enriched amorphous (6R) tetrahydrofolic acid with a chemical content of 63.3% and a (6R) percentage of 75.9, while in the other half of the mother liquor the pH is rapidly brought to 3.5 using 6.3 g of hydrochloric acid, resulting in enriched, amorphous (6R)-tetrahydrofolic acid with a chemical content of 64.8% and a (6R) percentage of 75.9.

Workup

customOne half of the mother liquor is precipitated with 1.1 g of ethanol
customgiving enriched amorphous (6R) tetrahydrofolic acid with a chemical content of 63.3%

Sources & evidence

ORD record: ord-ba13fb71265e44a3a2e367ba88d0b4bf
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271374B1

Reaction notes

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