Hydrochloric Acid → HCID 54058645, compound
Reaction equation
[OH-].[Li+].C[O:4][C:5]([CH:7]1[CH2:10][N:9]([C:11](=[O:26])[C@H:12]([CH2:24][OH:25])[NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:8]1)=[O:6].Cl.C(OCC)(=O)C>O.CO>[C:14]([NH:13][C@H:12]([C:11]([N:9]1[CH2:10][CH:7]([C:5]([OH:6])=[O:4])[CH2:8]1)=[O:26])[CH2:24][OH:25])([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
20 ml of a ca. 1M solution of lithium hydroxide in water was added to a stirred solution of 3.36 g of 1C in 100 ml of methanol at 0° C., and the mixture was stirred for 1.5 hours at 0° C. The mixture was neutralized (to pH 6-7) with 6N hydrochloric acid, the filtrate was stripped of solvent under reduced pressure and a temperature up to 55° C., and the residue was subjected to very low pressure (<1 Torr.). The residue was dissolved in 75 ml of methanol, 100 ml of ethyl acetate was added, the mixture was filtered, and the solvents were evaporated under reduced pressure. The residue was purified by flash chromatography, using a 2:1 v:v mixture of ethyl acetate and methanol as eluent. The solvents were evaporated and the residue was recrystallized from ethanol/ether, to give N-(N-carbobenzyloxy-L-seryl)-3-azetidinecarboxylic acid (1D) as a colorless hygroscopic solid, m.p.: 138°-143° C.
Workup
- customup to 55° C.
- filtrationthe mixture was filtered
- customthe solvents were evaporated under reduced pressure
- customThe residue was purified by flash chromatography
- additionv mixture of ethyl acetate and methanol as eluent
- customThe solvents were evaporated
- customthe residue was recrystallized from ethanol/ether
Sources & evidence
- ORD record
- ord-588add7a5c9146ccb799bcadb393ecc1
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04534787
Reaction notes
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