Ethyl phenylacetate → ethyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoate

HRID 2392923Notes

Reaction equation

HRID 2392923 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([CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:43]=[CH:42][CH:41]=[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:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:45]([O:47][CH2:48][CH3:49])=[O:46])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 7590Ethyl phenylacetateHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 36900245-(Carbobenzoxyamino)valeric acid

Product 1

HCID 18980739ethyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoateYield 42.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

The target compound was prepared as a pale yellow oil in an amount 3.8 g at a yield of 42.6% in the same manner as in Example 1 except that 5.7 g (22 mmol) of 5-(N-benzyloxycarbonylamino)pentanoic acid was dissolved in 23 ml of THF and 5.35 g (33 mmol) of CDI was dividedly added several times; 5.8 ml (44 mmol) of diisopropylamine and 10 ml of THF were added and 27.5 ml (44 mmol) of 1.63N BA solution was added dropwise; 6.6 ml (44 mmol) of ethyl phenylacetate instead of methyl phenylacetate was dissolved in 10 ml of THF; and 30 ml of saturated aqueous ammonium chloride solution was added to the reaction solution, the reaction was terminated, 50 g of 4N hydrochloric acid was added, and 100 ml of ethyl acetate was further added. The analytical results on the target compound are given below.

Workup

  1. addition27.5 ml (44 mmol) of 1.63N BA solution was added dropwise
  2. customthe reaction was terminated
  3. addition50 g of 4N hydrochloric acid was added
  4. addition100 ml of ethyl acetate was further added
  5. customThe analytical results on the target compound

Sources & evidence

ORD record
ord-56d8faf32eab4f528eb56dec71cf958c
Source dataset
uspto-grants-1998_09
Patent number
US05801271

Reaction notes

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