Triethylamine → (S)-4-(4-Fluorobenzyl)oxazolidine-2,5-dione

HRID 1693418Notes

Reaction equation

HRID 1693418 reaction equation
C([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>C(OCC)(=O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C@H:9]2[C:10](=[O:12])[O:11][C:6](=[O:5])[NH:8]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanine

Product 1

HCID 59753664(S)-4-(4-Fluorobenzyl)oxazolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2(S)-tert-butoxycarbonylamino-3-(4-fluorophenyl)propionic acid (1.5 g, 5.29 mmol) in ethyl acetate (100 mL) under an argon atmosphere was added triphosgene (628 mg, 2.12 mmol). To the solution was added triethylamine (0.8 mL 5.76 mmol,) over 1 min, and the reaction stirred for 72 h at rt. The reaction mixture was filtered, and the filtrate concentrated in vacuo to yield an oily residue. The crude material was crystallised from cold dichloromethane and petroleum ether to give the title compound. δH (CD3OD): 7.20 (2H, m), 7.10 (2H, m), 5.86 (1H, s, (NH)), 4.58 (1H, s), 3.33-3.23 (2H, m), 3.11-3.00 (1H, m).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto yield an oily residue
  4. customThe crude material was crystallised from cold dichloromethane and petroleum ether

Sources & evidence

ORD record
ord-5683c21807bd4b2d98167f5eb45077ba
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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