HCID 58293770, compound → HCID 67027086, compound

HRID 446718Notes

Reaction equation

HRID 446718 reaction equation
[CH2:1]([O:3][C:4]([N:6]([CH:13]([CH2:20][CH3:21])[CH2:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[CH2:7][C:8]([O:10]CC)=[O:9])=[O:5])[CH3:2]>CCO.[OH-].[Na+].O>[CH2:1]([O:3][C:4]([N:6]([CH2:7][C:8]([OH:10])=[O:9])[CH:13]([CH2:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[CH2:20][CH3:21])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 58293770HCID 58293770, compound

Product 1

HCID 67027086HCID 67027086, compoundYield 80.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

A solution of Compound 1035 (3.03 g, 9.668 mmol) in EtOH (50 mL) was treated with 1 M NaOH (48 mL) at RT overnight. The reaction mixture was diluted with 50 mL 1 M NaOH and 100 mL water, washed with EtOAc, and the aqueous layer was acidified with 6M HCl (30 mL) and extracted with EtOAc (2×). The organics were dried over Na2SO4, and the volatiles were evaporated under vacuum to give 2.23 g of (ethoxycarbonyl-(1-thiophen-2-ylmethyl-propyl)-amino)-acetic acid (Compound 1036).

Workup

  1. washwashed with EtOAc
  2. extractionextracted with EtOAc (2×)
  3. dry with materialThe organics were dried over Na2SO4
  4. customthe volatiles were evaporated under vacuum

Sources & evidence

ORD record
ord-2f54e2eb092c472e9486836a2e25ef51
Source dataset
uspto-grants-2013_07
Patent number
US08481524B2

Reaction notes

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