Tetrahydrofuran → HCID 18772239, compound

HRID 1154538Notes

Reaction equation

HRID 1154538 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][CH2:12][C:13]([OH:15])=[O:14].O1CCCC1.[C:21](=O)([O:27]C(C)(C)C)[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>[OH-].[Na+]>[C:23]([O:22][C:21]([N:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[CH2:12][C:13]([OH:15])=[O:14])=[O:27])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 457448Glycine, N-2-naphthalenyl-HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 18772239HCID 18772239, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
24 °C

Procedure

To a stirred solution of 10 g (50 mM) of 2-naphthylglycine (from Preparation 1) in 100 ml of 1N sodium hydroxide were added 50 ml of tetrahydrofuran followed by 30 g (140 mM) of di-tert.-butyl carbonate. The reaction mixture was stirred at 24° C. for four hours. The product was isolated by first washing the reaction mixture three times with 50 ml portions of diethyl ether, and then the mixture was made acidic to pH 2.0 by the addition of conc. hydrochloric acid. The aqueous acid mixture was extracted several times with ethyl acetate, and the extracts were combined, washed with water, dried and the solvent was removed by evaporation under reduced pressure to provide 12.8 g (85% yield) of N-tert.-butoxycarbonyl-2-naphthylglycine.

Workup

  1. customThe product was isolated
  2. washby first washing the reaction mixture three times with 50 ml portions of diethyl ether
  3. additionthe mixture was made acidic to pH 2.0 by the addition of conc. hydrochloric acid
  4. extractionThe aqueous acid mixture was extracted several times with ethyl acetate
  5. washwashed with water
  6. customdried
  7. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-fb1c5794a7884e4e86f87f256ab11b37
Source dataset
uspto-grants-1984_12
Patent number
US04490370

Reaction notes

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