Triethylamine → (s)-Methyl 2-oxooxazolidine-4-carboxylate

HRID 2306076

Reaction equation

HRID 2306076 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].C(N(CC)CC)C.Cl[C:18](Cl)([O:20]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[O:20]=[C:18]1[NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:9])[CH2:7][O:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 385463(s)-Methyl 2-oxooxazolidine-4-carboxylateYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of L-serine methyl ester hydrochloride (3.063 kg) in dichloromethane (24.1 L) at 0° C. was treated with triethylamine (5.908 kg), stirred for 30 minutes, treated with triphosgene (1.949 kg) in dichloromethane (5.356 kg) over 6.5 hours, stirred for 45 minutes, treated with hexanes (12.23 kg), stirred for 55 minutes, and filtered with ethyl acetate (16.013 kg). The filtrate was concentrated to provide a 35% (w/w) solution of the desired product (93.5%, 98% ee) in ethyl acetate. 1H NMR (300 MHz, CDCl3) δ6.55 (br s, 1H), 4.62 (dd, J=9, 9 Hz, 1H), 4.53 (dd, J=4, 9 Hz, 1H), 4.45 (dd, J=4, 9 Hz, 1H), 3.83 (s, 3H).

Workup

  1. stirringstirred for 45 minutes
  2. stirringstirred for 55 minutes
  3. filtrationfiltered with ethyl acetate (16.013 kg)
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3e6062d7936f4eb09bd6363d41f1b71f
Source dataset
uspto-grants-2002_08
Patent number
US06441189B1

Linked notes

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