Diisopropylamine → methyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-p-tolylheptanoate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.C(NC(C)C)(C)C.[C:38]1([CH3:49])[CH:43]=[CH:42][C:41]([CH2:44][C:45]([O:47][CH3:48])=[O:46])=[CH:40][CH:39]=1.[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:18])[CH:44]([C:41]1[CH:40]=[CH:39][C:38]([CH3:49])=[CH:43][CH:42]=1)[C:45]([O:47][CH3:48])=[O:46])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
The target compound was prepared as a pale yellow oil in an amount 12.9 g at a yield of 67.9% in the same manner as in Example 1 except that 12 g (47.8 mmol) of 5-(N-benzyloxycarbonylamino)pentanoic acid was dissolved in 60 ml of THF and 8.41 g (52.5 mmol) of CDI was added; 14.5 g (143 mmol) of diisopropylamine and 60 ml of THF were added and 89.5 ml (143 mmol) of 1.63N BA solution was added dropwise; 23.5 ml (143 mmol) of methyl p-tolylacetate instead of methyl phenylacetate was dissolved in 60 ml of THF; and 48 ml of saturated aqueous ammonium chloride solution was added to the reaction solution, the reaction was terminated, 100 g of 4N hydrochloric acid was added, and 240 ml of ethyl acetate was further added. The analytical results on the target compound are given below.
Workup
- addition89.5 ml (143 mmol) of 1.63N BA solution was added dropwise
- customthe reaction was terminated
- addition100 g of 4N hydrochloric acid was added
- addition240 ml of ethyl acetate was further added
- customThe analytical results on the target compound
Sources & evidence
- ORD record
- ord-18a8ac2b2f7f48eb848755e4d7a21212
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05801271
Reaction notes
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