4-Methylmorpholine → HCID 14158798, compound
Reaction equation
[C:1]([NH:8][C@@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.[NH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33]>C(Cl)Cl>[C:1]([NH:8][C@@H:9]([C:11]([NH:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])=[O:13])[CH3:10])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
18.9 Grams of Boc-D-alanine are dissolved in 100 ml of methylene chloride, and 22.0 ml of N-methylmorpholine is added. The solution is cooled to -70° C. and 13.0 ml of isobutylchloroformate is added. The reaction mixture is warmed to -15° C. and again cooled to -70° C. and 12.6 g of methyl glycinate hydrochloride is added. The reaction mixture is stirred for sixteen hours at room temperature then extracted three times with a 1.0 M solution of potassium bisulfate, saturated potassium bicarbonate solution, and a saturated sodium chloride solution. The methylene chloride solution is dried over anhydrous sodium sulfate, filtered and stripped of solvent. The product is purified by chromatography on silica gel using methanol-chloroform eluant. Removal of the solvent provides methyl Boc-D-alanylglycinate.
Workup
- temperatureThe reaction mixture is warmed to -15° C.
- temperatureagain cooled to -70° C.
- extractionthen extracted three times with a 1.0 M solution of potassium bisulfate, saturated potassium bicarbonate solution
- dry with materialThe methylene chloride solution is dried over anhydrous sodium sulfate
- filtrationfiltered
- customThe product is purified by chromatography on silica gel
- customRemoval of the solvent
Sources & evidence
- ORD record
- ord-b3c5214b0dc24feeb4e99223df7fc1f8
- Source dataset
- uspto-grants-1981_06
- Patent number
- US04273704
Reaction notes
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