Ammonium Hydroxide → Cytarabine

HRID 1284005Notes

Reaction equation

HRID 1284005 reaction equation

[CH:1]1[C:15](=[NH:16])[N:14]=[C:13]2[N:3]([C@@H:4]3[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@@H:5]3[O:12]2)[CH:2]=1.[OH-:17].[NH4+]>>[CH:1]1[C:15]([NH2:16])=[N:14][C:13](=[O:12])[N:3]([C@@H:4]2[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@@H:5]2[OH:17])[CH:2]=1

Participants

3

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 25051Ancitabine

Product 1

HCID 6253Cytarabine

Procedure

Cyclocytidine salt (8.0023 g., 18.25 mmole) and 80 ml. of 2N ammonium hydroxide are stirred at 58°. Hydrolysis is complete at 70 minutes.

Workup

customHydrolysis

Sources & evidence

ORD record: ord-64bb9ef04c02495c80c07a1f5c0369b1
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03978042

Reaction notes

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