Tetrahydrofuran → 2-(3-Tert-butoxycarbonylaminopropoxy)-4-methoxybenzoic acid

HRID 644272Notes

Reaction equation

HRID 644272 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:14]=1[C:15]([O:17]C)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1>O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:14]=1[C:15]([OH:17])=[O:16])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 68534059Methyl 2-(3-tert-butoxycarbonylaminopropoxy)-4-methoxybenzoate

Product 1

HCID 685323072-(3-Tert-butoxycarbonylaminopropoxy)-4-methoxybenzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

Methyl 2-(3-tert-butoxycarbonylaminopropoxy)-4-methoxybenzoate (18.61 g, 54.8 mmol) was suspended in 3:1 tetrahydrofuran:water (100 mL), then solid LiOH monohydrate (5.06 g, 121 mmol) was added and the mixture was stirred at 50° C. for 24 hours. The mixture was diluted with water (350 mL) and washed with diethyl ether (2×250 mL). The aqueous layer was acidified to pH 1-2 with 1 N sodium bisulfate and the resulting slurry was extracted with EtOAc (2×300 mL). The combined EtOAc layers were washed with brine, dried, then concentrated in vacuo to give a solid white mass. Recrystallization from EtOAc provided 2-(3-tert-butoxycarbonylaminopropoxy)-4-methoxybenzoic acid as white needles (15.52 g, 87%).

Workup

  1. washwashed with diethyl ether (2×250 mL)
  2. extractionthe resulting slurry was extracted with EtOAc (2×300 mL)
  3. washThe combined EtOAc layers were washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give a solid white mass
  7. customRecrystallization from EtOAc

Sources & evidence

ORD record
ord-52ca2586607145cb8766981d405dc947
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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