Ethyl phenylacetate → ethyl 7-(N-t-butoxycarbonylamino)-3-oxo-2-phenylheptanoate
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.C(NC(C)C)(C)C.[C:35]1([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[Cl-].[NH4+]>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:15])[CH:41]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
The target compound was prepared as a pale yellow oil in an amount 7.8 g at a yield of 48.1% in the same manner as in Example 1 except that 10 g (45.8 mmol) of 5-(N-t-butoxycarbonylamino)pentanoic acid instead of 5-(N-benzyloxycarbonylamino)pentanoic acid was dissolved in 70 ml of THF and 11.1 g (68.7 mmol) of CDI was added; 9.5 ml (72 mmol) of diisopropylamine and 40 ml of THF were added and 42 ml (69 mmol) of 1.63N BA solution was added dropwise; 10.6 g (68.7 mmol) of ethyl phenylacetate instead of methyl phenylacetate was dissolved in 20 ml of THF; and 30 ml of saturated aqueous ammonium chloride solution was added to the reaction solution, the reaction was terminated, 70 g of 4N hydrochloric acid was added, and 100 ml of ethylacetate was further added. The analytical results on the target compound are given below.
Workup
- addition42 ml (69 mmol) of 1.63N BA solution was added dropwise
- customthe reaction was terminated
- addition70 g of 4N hydrochloric acid was added
- addition100 ml of ethylacetate was further added
- customThe analytical results on the target compound
Sources & evidence
- ORD record
- ord-944cf6afc84243aabc045cc0a12c1acd
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05801271
Reaction notes
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