Sodium Carbonate → Benzyl L-leucinate
Reaction equation
C(=O)([O-])[O-].[Na+].[Na+].N[C@H](C(NCC(NCC(N[C@H](C([NH:45][C@H:46]([C:51]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52])[CH2:47][CH:48]([CH3:50])[CH3:49])=O)CC1C=CC=CC=1)=O)=O)=O)CC1C=CC(OCC2C=CC=CC=2)=CC=1.N[C@H](C(O)=O)CC1C=CC(OCC2C=CC=CC=2)=CC=1>>[NH2:45][C@H:46]([C:51]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52])[CH2:47][CH:48]([CH3:50])[CH3:49]Participants
Procedure
On the other hand, the filtrate and the washing liquid were well washed with chlorobenzene (5 ml) and then combined with each other, thereby a clear solution was obtained. When 10% aqueous sodium carbonate solution (12 ml) was added to the solution, a solid was deposited. After the mixture was allowed to mature by stirring at room temperature for 1 hour and then under ice-cooling for 1 hour, the deposited solid was filtered, and sequentially washed with chlorobenzene (2 ml) and water (2 ml), and dried under vacuum, thereby a white solid was obtained. The purity of the target Tyr(Bn)-Gly-Gly-Phe-Leu-OBn (SEQ ID NO: 2) was 88%, and the content of Tyr(Bn) was 4.9%. Further, the crystallization yield was 88%, and the acquisition yield relative to the Leu-OBn.TsOH salt was 58%.
Workup
- washOn the other hand, the filtrate and the washing liquid were well washed with chlorobenzene (5 ml)
- customwas obtained
- temperatureunder ice-cooling for 1 hour
- filtrationthe deposited solid was filtered
- washsequentially washed with chlorobenzene (2 ml) and water (2 ml)
- customdried under vacuum
- customa white solid was obtained
- customFurther, the crystallization yield was 88%
Sources & evidence
- ORD record
- ord-755144f8cb54443fac184f06a63c6bcf
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346850B2
Reaction notes
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