Hydrochloric Acid → S-Adenosylhomocysteine
Reaction equation
[Na+].[NH2:2][C@H:3]([C:7]([O-:9])=[O:8])[CH2:4][CH2:5][SH:6].Cl.Cl.ClC[CH:14](O)[C@H:15]1[O:19][C@@H:18]([N:20]2[C:29]3[N:28]=[CH:27][N:26]=[C:24]([NH2:25])[C:23]=3[N:22]=[CH:21]2)[C@H:17]([OH:30])[C@@H:16]1[OH:31].[I-].[K+]>>[C@@H:18]1([N:20]2[C:29]3[N:28]=[CH:27][N:26]=[C:24]([NH2:25])[C:23]=3[N:22]=[CH:21]2)[O:19][C@H:15]([CH2:14][S:6][CH2:5][CH2:4][C@@H:3]([C:7]([OH:9])=[O:8])[NH2:2])[C@@H:16]([OH:31])[C@H:17]1[OH:30]Participants
Conditions
- Temperature
- 10 °C
Procedure
L-Homocysteine sodium salt solution (850 Kg), prepared as described above, was cooled to 10° C. and dil.hydrochloric acid (1:1; 100 Lit) was added til the pH became 11.3 to 11.5. To this solution, 5′-Chloromethyl adenosine hydrochloride (135 Kg) and potassium iodide (13.5 Kg) were added and stirred at 70-80° C. for 5 h. The reaction was monitored by HPLC and cooled to 15° C. Dil.hydrochloric acid (1:1; 200 Lit) was added to bring down the pH to 2.0. Activated carbon (10 Kg) was added, stirred for 30 min and filtered. To the mother liquor, ammonia solution (15%) was added to set the pH to 6.0-6.2. The precipitate was stirred at 20° C. for 24 h and filtered. The solid was washed two times with water (200 Lit). The wet cake was dried at 40° C. under vacuum.
Workup
- temperaturecooled to 15° C
- additionActivated carbon (10 Kg) was added
- stirringstirred for 30 min
- filtrationfiltered
- additionTo the mother liquor, ammonia solution (15%) was added
- stirringThe precipitate was stirred at 20° C. for 24 h
- filtrationfiltered
- washThe solid was washed two times with water (200 Lit)
- customThe wet cake was dried at 40° C. under vacuum
Sources & evidence
- ORD record
- ord-d5a1a4f1409d4e788a581ba2cdbddb11
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06881837B2
Reaction notes
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