Triethylamine → HCID 42643275, compound
Reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:10](C(O)=O)[CH2:9][N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:7]1)=[O:5])[CH3:2].C([N:23]([CH2:26]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.[CH3:45][Si:46]([CH3:51])([CH3:50])[CH2:47][CH2:48][OH:49]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:10]([NH:23][C:26]([O:49][CH2:48][CH2:47][Si:46]([CH3:51])([CH3:50])[CH3:45])=[O:35])[CH2:9][N:8]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:7]1)=[O:5])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
40.1 (3R,4R)-Pyrrolidine-1,3,4-tricarboxylic acid 1-tert.-butyl ester 3-ethyl ester (CAS 595556-31-35 g; 17 mmol) was dissolved in toluene (50 ml), triethylamine (2.43 ml; 17 mmol) and diphenylphosphoryl azide (3.77 ml; 17 mmol) were added. The reaction mixture was stirred at 80° C. for 30 min. After that 2-(trimethylsilyl)ethanol (12.41 ml; 87 mmol) was added and the reaction mixture was stirred at 90° C. for 14 h. The reaction mixture was evaporated, dissolved in ethyl acetate and extracted with aqueous Na2CO3 and aqueous HCl (1N). The organic layers were combined and dried over Na2SO4. Flash chromatography over silica gel using DCM/MeOH/NH3 as eluent yielded 4.6 g (65.6%) (3S,4R)-4-(2-trimethylsilanyl-ethoxycarbonylamino)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester. MS 403.5 [M+H+].
Workup
- stirringthe reaction mixture was stirred at 90° C. for 14 h
- customThe reaction mixture was evaporated
- dissolutiondissolved in ethyl acetate
- extractionextracted with aqueous Na2CO3 and aqueous HCl (1N)
- dry with materialdried over Na2SO4
Sources & evidence
- ORD record
- ord-a82ddb0237da4def9f9bd1357179f5c7
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820699B2
Reaction notes
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