Sulfuric Acid → (S)-3-(4-(Benzyloxy)phenyl)-2-ethoxypropanoic acid

HRID 891254Notes

Reaction equation

HRID 891254 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([O:29][CH2:30][CH3:31])[C:17](N[C@H](C2C=CC=CC=2)CO)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:32]S(O)(=O)=O.[OH-].[Na+]>O1CCOCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@H:16]([O:29][CH2:30][CH3:31])[C:17]([OH:18])=[O:32])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 117615803-(4-benzyloxyphenyl)-(S)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amide

Product 1

HCID 11044786(S)-3-(4-(Benzyloxy)phenyl)-2-ethoxypropanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

(2S)-3-[4-(benzyloxy)phenyl]-2-ethoxy-N-[(1R)-2-hydroxy-1-phenylethyl ]propanamide (4.3 kg, 10.2 mol) were dissolved in dioxane (30 L) and diluted with deionized water (35 L). To this opaque reaction mixture, H2SO4 (19.2 kg, 192 mol) was added. The reaction temperature was raised to 80° C. and kept at 80° C. for 15 hours. The reaction mixture was extracted twice with TBME (64 L, 70 L) at room temperature. The combined organic phases were extracted twice with 1 M NaOH (2×20 L, 2×20 mol). The aqueous phases were acidified with H2SO4 (24 L, 24 mol), extracted with TBME (40 L) and the organic phases dried with saturated NaCl solution. The solution was concentrated to yield 64 L concentrate which contained 2.9 kg, 100% (GLC 68% area (2S)-3-[4-(benzyloxy) phenyl]-2-ethoxypropanoic acid and 28% area (2S)-2-ethoxy-(4-hydroxyphenyl) propanoic acid).

Workup

  1. additionwas added
  2. extractionThe reaction mixture was extracted twice with TBME (64 L, 70 L) at room temperature
  3. extractionextracted with TBME (40 L)
  4. dry with materialthe organic phases dried with saturated NaCl solution
  5. concentrationThe solution was concentrated
  6. customto yield 64 L
  7. concentrationconcentrate which

Sources & evidence

ORD record
ord-c72501376e55461889267f847010a8f7
Source dataset
uspto-grants-2006_02
Patent number
US07002037B2

Reaction notes

Loading…