Water → (3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic Acid
Reaction equation
C(OC(N1CC[C@@H](NC2C=CC(N3C[C@H](CNC(=O)C)OC3=O)=CC=2F)C1)=O)(C)(C)C.C([O:34][C:35]([C@H:37]1[C@@H:41]([CH2:42][NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][N:39]([CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH2:38]1)=[O:36])C.O.[OH-].[Li+].O>C1COCC1>[CH2:51]([N:39]1[CH2:40][C@H:41]([CH2:42][NH:43][C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])[C@H:37]([C:35]([OH:36])=[O:34])[CH2:38]1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1Participants
6
Reactant 4
HCID 962Water
HCID 168937Lithium hydroxide, monohydrate
HCID 67274345(3R)3-{4-[(5S)-5-(Acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenylamino}-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester
HCID 68420071(3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic Acid Ethyl EsterProduct 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of 2.9 (3R, 4R) and (3S, 4S)-1-benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic acid ethyl ester (8.0 mmol) in 50 ml THF were added 671 mg lithium hydroxide mono hydrate (, 16 mmol) and 0.5 ml water. The solution was stirred at 40° C. and the reaction monitored by TLC. After 72 h the solvent was evaporated, the residue dissolved in dichloromethane, washed with water and brine, dried over Mg sulfate, filtered and evaporated. The residue was crystallized from a dichloromethane/hexane mixture.
Workup
- customAfter 72 h the solvent was evaporated
- dissolutionthe residue dissolved in dichloromethane
- washwashed with water and brine
- dry with materialdried over Mg sulfate
- filtrationfiltered
- customevaporated
- customThe residue was crystallized from a dichloromethane/hexane mixture
Sources & evidence
- ORD record
- ord-f406e256d96646acb6282da856e4a168
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329908B2
Reaction notes
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