Tetrahydrofuran → 2-{[(tert-Butoxycarbonyl)amino]methyl}-3-(4-chlorophenyl)propanoic acid

HRID 387515Notes

Reaction equation

HRID 387515 reaction equation
O[Li].O.[C:4]([O:8][C:9]([NH:11][CH2:12][CH:13]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:14]([O:16]C)=[O:15])=[O:10])([CH3:7])([CH3:6])[CH3:5].C1COCC1>O>[C:4]([O:8][C:9]([NH:11][CH2:12][CH:13]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:14]([OH:16])=[O:15])=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 44890986Methyl 2-{[(tert-butoxycarbonyl)amino]methyl}-3-(4-chlorophenyl)propanoate

Product 1

HCID 448909682-{[(tert-Butoxycarbonyl)amino]methyl}-3-(4-chlorophenyl)propanoic acidYield 87.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

LiOH—H2O (0.09 g, 2.1 mmol) was added to a solution of methyl 3-(tert-butoxycarbonylamino)-2-(4-chlorobenzyl)propanoate (0.64 g, 1.9 mmol) in 2:1 THF:H2O (20 mL). The reaction was then stirred for 3 hours at room temperature and then diluted with H2O (50 mL) and washed with ether (50 mL). The aqueous layer was next acidified with solid KHSO4, saturated with solid NaCl, and extracted with DCM. The combined organic extracts were dried (Na2SO4), filtered, concentrated, and dried in vacuo to give 3-(tert-butoxycarbonylamino)-2-(4-chlorobenzyl)propanoic acid (0.523 g, 85%) as a solid. MS ESI (−) m/z 312 detected.

Workup

  1. washwashed with ether (50 mL)
  2. extractionextracted with DCM
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-663b7123b3724ecf9947f1b356833cbc
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

Loading…