Tributylamine → N-Acetylcarnosine
Reaction equation
[OH2:1].Cl.[NH2:3][C@H:4]([C:11]([OH:13])=[O:12])[CH2:5][C:6]1[N:10]=[CH:9][NH:8][CH:7]=1.[OH-].[Na+].[CH2:16]([C:20](C)=[O:21])[CH:17](C)C.[CH2:23]([N:27](CCCC)CCCC)[CH2:24]CC>O>[CH3:24][C:23]([NH:27][CH2:17][CH2:16][C:20]([NH:3][C@H:4]([C:11]([OH:13])=[O:12])[CH2:5][C:6]1[NH:10][CH:9]=[N:8][CH:7]=1)=[O:21])=[O:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
On the other hand, 52.4 g of L-histidine hydrochloride monohydrate was dissolved in 400 ml of water and the solution was adjusted to pH 10.5 with about 112 ml of 4 N aqueous sodium hydroxide solution. To this solution were simultaneously added dropwise 370 ml of methyl isobutyl ketone solution containing 148.6 g of tri-n-butylamine salt of 3-acetylaminopropionic acid-sulfuric acid mixed acid anhydride which has been prepared previously and 330 ml of 4 N aqueous sodium hydroxide solution while the reaction medium was stirred and maintained to a pH of 10.3-10.5 and a temperature of 5°-10° C. After stirring for 30 minutes at room temperature, the reaction was adjusted to pH 13.0 with about 300 ml of 4 N aqueous sodium hydroxide solution and allowed to stand. The upper methyl isobutyl ketone layer was separated out and the lower aqueous layer was treated by a similar manner as in Example 4 to obtain 49.6 g of N-acetyl-L-carnosine crystals.
Workup
- customhas been prepared previously
- temperaturemaintained to a pH of 10.3-10.5
- customa temperature of 5°-10° C
- customThe upper methyl isobutyl ketone layer was separated out
- additionthe lower aqueous layer was treated by a similar manner as in Example 4
Sources & evidence
- ORD record
- ord-9dd8eec9b41b4f58bdeb24c17d6523d5
- Source dataset
- uspto-grants-1983_06
- Patent number
- US04387232
Reaction notes
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