2,3-Dihydroxybutanedioic Acid → HCID 131710296, compound
Reaction equation
[NH2:1][C@H:2]1[C:14](=[O:15])[N:4]2[C:5]([C:11]([O-:13])=[O:12])=[C:6]([CH2:9][CH3:10])[CH2:7][S:8][C@H:3]12.C(O)(=O)[CH:17]([CH:19]([C:21](O)=O)O)O.[CH3:26]O>>[NH2:1][C@H:2]1[C:14](=[O:15])[N:4]2[C:5]([C:11]([O:13][C:19]([CH3:17])([CH3:21])[CH3:26])=[O:12])=[C:6]([CH2:9][CH3:10])[CH2:7][S:8][C@H:3]12Participants
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 2.84 g of tert.-butyl DL cis 7-amino-3-ethyl-3-cepheme-4-carboxylate, 1.65 g of D(-) tartaric acid and 8 ml of methanol was heated to 60°C and the temperature was returned to room temperature and held at 18°C for 10 minutes. The mixture was vacuum filtered and the precipitate was washed with a 1-1 methanol-ether mixture and then with ether and dried. The residue was then dissolved in 25ml of aqueous 10% sodium bicarbonate and 15 ml of methylene chloride and the organic phase was decanted. The aqueous phase was reextracted with methylene chloride and the combined organic phases were dried over magnesium sulfate and evaporate to dryness. The residue was taken up in ether and the mixture was vacuum filtered to obtain 1.19 g of the L (+) enantiomorph of tert.-butyl cis 7-amino-3-ethyl-3-cepheme-4-carboxylate melting at 120°C and having a specific rotation [α]D20 = + 74° ± 2.5° (c = 0.5% in chloroform).
Workup
- customwas returned to room temperature
- filtrationfiltered
- washthe precipitate was washed with a 1-1 methanol-ether mixture
- dry with materialwith ether and dried
- dissolutionThe residue was then dissolved in 25ml of aqueous 10% sodium bicarbonate and 15 ml of methylene chloride
- customthe organic phase was decanted
- dry with materialthe combined organic phases were dried over magnesium sulfate
- customevaporate to dryness
- filtrationfiltered
Sources & evidence
- ORD record
- ord-29e2c4e264cf4223aeb959d4e0821237
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03962223
Reaction notes
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