Sodium Carbonate → (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C@H:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[C:23](Cl)([O:25][CH2:26][CH:27]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24]>O.O1CCOCC1>[CH:38]1[C:39]2[CH:27]([CH2:26][O:25][C:23]([N:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C@H:10]3[C:14]([OH:16])=[O:15])=[O:24])[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:34]=2[CH:35]=[CH:36][CH:37]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred mixture of (S)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (1.0 g, 4.34 mmol) and Na2CO3 (0.90 g, 10.80 mmol) in water (10 mL) was added solution of FMOC-Cl (1.23 g, 4.77 mmol) in 1,4-dioxane (10 mL) dropwise at 0° C. The reaction mixture was stirred at room temperature for 16 h then diluted with water (50 mL) and washed with MTBE (25 mL). The aqueous layer was acidified with 1N aqueous HCl (10 mL) to pH 2 and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with brine solution (50 mL), dried over anhydrous Na2SO4, filtered and concentrated to afford the title compound (0.87 g) as an off-white solid. The crude product was used in the next step without purification.
Workup
- washwashed with MTBE (25 mL)
- extractionextracted with EtOAc (3×50 mL)
- washThe combined organic extracts were washed with brine solution (50 mL)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-58ff00aa787c42c2ab8096240564f92b
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133147B2
Reaction notes
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