Hydrochloric Acid → HCID 13216876, compound

HRID 1790860Notes

Reaction equation

HRID 1790860 reaction equation
[C:1](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[NH2:17][C@H:18]([C:20]([O-:22])=[O:21])[CH3:19].Cl>C(O)C.C(OC([C@@H](N[C@H](C(O)=O)C)CC(=O)C1C=CC=CC=1)=O)C>[CH2:14]([O:13][C:11]([CH:10]([NH:17][C@H:18]([C:20]([OH:22])=[O:21])[CH3:19])[CH2:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:12])[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5369605Ethyl (2E)-4-oxo-4-phenyl-2-butenoateHCID 23721940HCID 23721940, compound

Product 1

HCID 13216876HCID 13216876, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 10913373HCID 10913373, compoundCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of 25.9 g of ethyl trans-β-benzoylacrylate in 770 ml of ethanol was added a solution of 6.03 g of L-alanine lithium salt in 426 ml of ethanol over 30 minutes at room temperature. After completion of addition, the mixture was stirred for an additional 5 minutes, and then 5.29 ml of concentrated hydrochloric acid was added, followed by cooling with ice-water. As seed crystals, 679 mg of N-(1(S)-ethoxycarbonyl-3-oxo-3-phenylpropyl)-L-alanine was added, and the mixture was stirred for 4 hours. The crystals separating out were collected by filtration, washed with ethanol, and dried, whereby 12.7 g of N-(1-ethoxycarbonyl-3-oxo-3-phenylpropyl)-L-alanine (1S/1R ratio=95/5) was obtained.

Workup

  1. additionAfter completion of addition
  2. stirringthe mixture was stirred for 4 hours
  3. customThe crystals separating out
  4. filtrationwere collected by filtration
  5. washwashed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-0bbaa1dd2d284674aff4b80eef62d499
Source dataset
uspto-grants-2006_07
Patent number
US07071349B2

Reaction notes

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