(2R)-2-((2-(tert-butoxycarbonylamino)ethyl)amino)-3-(2-naphthyl)propionic acid methylester → (R)-3-(Naphthalen-2-ylmethyl)piperazin-2-one
Reaction equation
COC(=O)[C@H:4]([NH:16][CH2:17][CH2:18][NH:19][C:20]([O:22]C(C)(C)C)=O)[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[CH:15][C:6]=1[CH2:5][C@H:4]1[NH:16][CH2:17][CH2:18][NH:19][C:20]1=[O:22]Participants
4
Procedure
##STR197## (2R)-2-((2-(tert-butoxycarbonylamino)ethyl)amino)-3-(2-naphthyl)propionic acid methylester (3.4 g, 9.1 mmol) was stirred for 1 h in a mixture of TFA (5 ml) and methylene chloride(5 ml). The volatiles were removed in vacuo and the residue was dissolved in a mixture of water (40 ml) and methanol (100 ml). Sodium hydrogencarbonate (2.3 g) was added and the mixture was stirred overnight. The solvent was removed in vacuo and the residue was dissolved in water (40 ml) and extracted with ethyl acetate (10×50 ml). The combined organic phases were dried (magnesium sulphate) and the solvent was removed in vacuo to afford 1.96 g of (3R)-3-((2-naphthyl)methyl)piperazin-2-one.
Workup
- customThe volatiles were removed in vacuo
- dissolutionthe residue was dissolved in a mixture of water (40 ml) and methanol (100 ml)
- additionSodium hydrogencarbonate (2.3 g) was added
- customThe solvent was removed in vacuo
- dissolutionthe residue was dissolved in water (40 ml)
- extractionextracted with ethyl acetate (10×50 ml)
- dry with materialThe combined organic phases were dried (magnesium sulphate)
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-fb970d093fcb4b94a7d9f16e7eac3a31
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05922770
Reaction notes
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