Hydrochloric Acid → N-(glutaminyl-serinyl)leucine benzyl ester hydrochloride
Reaction equation
[CH2:1]([O:8][C:9](=[O:38])[C@H:10]([CH2:34][CH:35]([CH3:37])[CH3:36])[NH:11][C:12](=[O:33])[C@H:13]([CH2:31][OH:32])[NH:14][C:15](=[O:30])[C@H:16]([CH2:18][CH2:19][C:20](=[O:29])[NH:21]C(OC(C)(C)C)=O)[NH2:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:39]>>[ClH:39].[CH2:1]([O:8][C:9](=[O:38])[C@H:10]([CH2:34][CH:35]([CH3:36])[CH3:37])[NH:11][C:12](=[O:33])[C@H:13]([CH2:31][OH:32])[NH:14][C:15](=[O:30])[C@H:16]([CH2:18][CH2:19][C:20](=[O:29])[NH2:21])[NH2:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
3
Procedure
N-(N′-(Boc)-glutaminyl-serinyl)leucine benzyl ester (715 g, 1.33 M) (prepared as described in Step 2) was suspended in iPAC (3.5 L) at room temperature. To the slurry was added a 3.8 M solution of HCl in iPAC (3.5 L, 13.3 M) whereupon all the solids dissolved. After a short time, the product crystallised. The mixture was stirred at room temperature for 3.75 hours when HPLC showed complete reaction. The slurry was diluted with iPAC (4.0 L), stirred for 1 hour at room temperature and the solid collected by filtration under nitrogen. The product is very hygroscopic in the presence of excess HCl and must be collected under dry nitrogen.
Workup
- customwas suspended in iPAC (3.5 L) at room temperature
- dissolutiondissolved
- customAfter a short time, the product crystallised
- customreaction
- additionThe slurry was diluted with iPAC (4.0 L)
- stirringstirred for 1 hour at room temperature
- filtrationthe solid collected by filtration under nitrogen
- custommust be collected under dry nitrogen
Sources & evidence
- ORD record
- ord-d0b2753dbd1049fc9fb5ca813ae51f99
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06552166B1
Reaction notes
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