Ethanol → HCID 66762188, compound

HRID 561894Notes

Reaction equation

HRID 561894 reaction equation
CCO.[C:4]([O:8][C:9]([NH:11][CH2:12][CH:13]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][OH:29])=[CH:22][CH:21]=1)[C:14]([O:16]CC)=[O:15])=[O:10])([CH3:7])([CH3:6])[CH3:5].[Li+].[OH-]>C1COCC1>[C:4]([O:8][C:9]([NH:11][CH2:12][CH:13]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][OH:29])=[CH:22][CH:21]=1)[C:14]([OH:16])=[O:15])=[O:10])([CH3:5])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 66761780HCID 66761780, compound

Product 1

HCID 66762188HCID 66762188, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 5:3 (v/v) solution of EtOH and THF (0.2 M) of ethyl 3-[(tert-butoxycarbonyl)amino]-2-[4-(2-hydroxyethoxy)benzyl]propanoate from the previous step (1 eq.) was added LiOH (1 M aqueous solution, 2 eq.). The resulting mixture was stirred at RT for 48 h. Following the removal of the volatiles in vacuo, the resulting residue was partitioned between ether and 1 N aq. NaOH. The aqueous layer was separated and washed further with ether. The aqueous layer was then acidified to pH ˜2 with conc. HCl and the resulting suspension extracted with dichloromethane. The combined dichloromethane extracts was concentrated in vacuo. The crude product thus obtained was recrystallized from EtOAc-hexane to afford the title compound as a white solid.

Workup

  1. customthe removal of the volatiles in vacuo
  2. customthe resulting residue was partitioned between ether and 1 N aq. NaOH
  3. customThe aqueous layer was separated
  4. washwashed further with ether
  5. extractionthe resulting suspension extracted with dichloromethane
  6. concentrationThe combined dichloromethane extracts was concentrated in vacuo
  7. customThe crude product thus obtained
  8. customwas recrystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-3ca49de460ee4937b48b0784580b4b76
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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