Triethylamine → Methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-(4-hydroxyphenyl)acetate

HRID 454970

Reaction equation

HRID 454970 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:13])[C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:6].[C:14](=O)([O-:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O:23]C(C)(C)C.C(N(CC)CC)C>O1CCCC1>[CH3:2][O:3][C:4](=[O:13])[C@H:5]([NH:6][C:14]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([OH:23])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12247453D-Phenylglycine methyl ester hydrochlorideHCID 52911111Di-tert-butyl di-carbonate

Product 1

HCID 10934864Methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-(4-hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(R)-(−)-2-phenylglycine methyl ester hydrochloride (2.17 g, 10 mmol) and di-t-butyl di-carbonate (2.62 g, 12 mmol) were combined in tetrahydrofuran (100 ml). Triethylamine (1.60 ml, 22 mmol) was added to the mixture via syringe at room temperature. The reaction mixture was stirred at room temperature overnight. The THF in reaction mixture was then removed in vacuum. Saturated aqueous NH4Cl and ethyl acetate were added to the mixture in a separatory funnel. The aqueous layer was extracted with ethyl acetate (3×40 ml). The combined organic layer was washed with saturated aqueous NH4Cl, dried over MgSO4, filtered and concentrated to give a white solid (3.08 g, crude product): 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.20 (d, J=8.1 Hz, 2H), 6.77 (m, 2H), 5.73 (br. s., 1H), 5.56 (br. s., 1H), 5.25 (d, J=6.6 Hz, 1H), 3.73 (s, 3H), 1.46 (s, 9H) LCMS (ESI) m/e 282.1 [(M+H)+, calcd for C14H20NO5 282.3].

Workup

  1. customwas then removed in vacuum
  2. additionSaturated aqueous NH4Cl and ethyl acetate were added to the mixture in a separatory funnel
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×40 ml)
  4. washThe combined organic layer was washed with saturated aqueous NH4Cl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a white solid (3.08 g, crude product)

Sources & evidence

ORD record
ord-3ca3b1e1dee741089f826942e7eb8ff0
Source dataset
uspto-grants-2013_07
Patent number
US08497271B2

Linked notes

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