Disodium 2,3-dihydroxybutanedioate → HCID 45091916, compound
Reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[CH2:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=O)C.CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[C:14]([O:13][C:11](=[O:12])[NH:10][CH2:9][C@@H:7]1[CH2:8][C@H:6]1[CH:4]=[O:3])([CH3:15])([CH3:17])[CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of Trans-2-(tert-Butoxycarbonylamino-methyl)-cyclopropanecarboxylic acid ethyl ester (0.320 g, 1.3 mmol), in toluene (5 mL) at −78° C. a 1.2M solution of DIBAL-H (1.86 mL, 2.2 mmol) in toluene was added. The mixture was stirred at −78° C. until TLC after 0.5 h indicated completion of the reaction. A saturated solution of sodium tartrate was added and the water was extracted three times with dichloromethane. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and evaporated. The crude product was used without purification on the next step. MS (m/e): 200.3 (M+H+)
Workup
- customcompletion of the reaction
- extractionthe water was extracted three times with dichloromethane
- washThe combined organic layers were washed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe crude product was used without purification on the next step
Sources & evidence
- ORD record
- ord-42b0c9bdafab49f2a8733970544f1492
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415350B2
Reaction notes
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