Water → 2-{[(Benzyloxy)carbonyl]amino}hexanedioic acid
Reaction equation
[CH2:1]([CH2:8][C:9]([OH:11])=[O:10])[CH2:2][C@H:3]([NH2:7])[C:4]([OH:6])=[O:5].C(N(CC)CC)C.O.[CH2:20]([O:27][C:28](ON1C(=O)CCC1=O)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCOCC1>[CH2:20]([O:27][C:28]([NH:7][CH:3]([CH2:2][CH2:1][CH2:8][C:9]([OH:11])=[O:10])[C:4]([OH:6])=[O:5])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of L-2-aminoadipic acid (920 mg, 5.71 mmol), triethylamine (2.85 mL, 20.5 mmol) and water (3 mL) in 12 mL of dioxane was cooled to 0° C. and N-benzyloxycarbonyloxysuccinimide (Cbz-OSu: 1.71 g, 6.85 mmol) was added. The reaction mixture was stirred at 0° C. for 2 hours and at ambient temperature for 0.5 hours. The reaction mixture was washed with ethyl acetate and then acidified with aqueous potassium hydrogen sulfate. The acidic solution was extracted with ethyl acetate and the ethyl acetate solution was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 1.80 g of the title compound. MS (FAB+) m/e 296 (M+H)+.
Workup
- washThe reaction mixture was washed with ethyl acetate
- extractionThe acidic solution was extracted with ethyl acetate
- washthe ethyl acetate solution was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-cacd9f9a6d934fbf81753716232a4ea4
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05270302
Reaction notes
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