Sodium Chloride → HCID 11862697, compound
Reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[CH2:11])[CH2:8][C@H:7]1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Na+].[Cl-].[OH-].[Na+]>>[CH2:15]([O:14][C:12]([C@H:7]1[CH2:8][C:9](=[CH2:11])[CH2:10][C@@H:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:13])[CH3:16]Participants
Conditions
- Temperature
- 7 °C
Procedure
An emulsion of 1.1 g racemic trans-4-Methylene-cyclopentane-1,2-dicarboxylic acid diethyl ester (Merck 8.14188.0010) in an aqueous buffer (potassium phosphate 5 mM, NaCl 0.1 M) was adjusted to pH 7.0. Under stirring at 7° C. the hydrolysis was performed with 14 mg lipase PN from Phycomyces nitens [Wako Chemicals GmbH Nissanstrasse 2 D-41468 Neuss Germany; catalog # 122-02651] under pH control (pH-stat, 1M NaOH). After consumption of 2.4 ml 1 M NaOH solution within 24 h the reaction mixture was extracted twice with 250 ml t-butyl methyl ether. The organic phase was subsequently washed with 250 ml saturated sodium bicarbonate and 250 ml saturated NaCl solution. Evaporation and drying in vacuo overnight yielded 0.49 g of the title compound 41a. MS: 226.0 (M)+; chiral GC: ee >99% (BGB-175, 30 m×0.25 mm; H2, 120 kPa, Split 1/20; 100-180° C., 2° C./min; Inj.-T.: 200° C.; Dect.-T.: 220° C.).
Workup
- customAfter consumption of 2.4 ml 1 M NaOH solution within 24 h the reaction mixture
- extractionwas extracted twice with 250 ml t-butyl methyl ether
- washThe organic phase was subsequently washed with 250 ml saturated sodium bicarbonate and 250 ml saturated NaCl solution
- customEvaporation
- customdrying in vacuo overnight
Sources & evidence
- ORD record
- ord-9171da76c4674278a26445b9f01b58ab
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07501413B2
Reaction notes
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