(S)-(+)-3-(Benzyloxycarbonyl)-5-oxo-4-oxazolidinepropionic acid → (S)-5-oxo-3-[(phenylmethoxy)carbonyl]-4-Oxazolidinepropanal

HRID 1077965Notes

Reaction equation

HRID 1077965 reaction equation
[O:1]=[C:2]1[O:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@H:3]1[CH2:17][CH2:18][C:19](O)=[O:20].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C1COCC1.C(Cl)Cl>[O:1]=[C:2]1[O:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[C@H:3]1[CH2:17][CH2:18][CH:19]=[O:20]

Participants

5

Reactant 2

HCID 688249(S)-(+)-3-(Benzyloxycarbonyl)-5-oxo-4-oxazolidinepropionic acidHCID 178418287HCID 178418287, compound

Product 1

HCID 11022192(S)-5-oxo-3-[(phenylmethoxy)carbonyl]-4-OxazolidinepropanalYield 51.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 27 g (92.7 mmol) of the crude acid (43c) in 200 mL of THF is cooled to 0° C. and 13 mL (10.7 g, 141 mmol) of borane-methyl sulfide complex is added dropwise via an addition funnel. The reaction is allowed to warm gradually to room temperature and stirred for 12 h. The resulting mixture is concentrated in vacuo to give a white glassy material which is taken up in 500 mL of methylene chloride and treated with of pyridinium chlorochromate (61 g, 281 mmol) at 0° C. in the presence of 3 -- molecular sieve. The mixture is allowed to warm to room temperature and stirred for 3 h. The mixture is filtered through diatomaceous earth with ether (200 mL) then concentrated. The residue is taken up in ether and filtered again through diatomaceous earth with ether then concentrated to give 13.22 g of the crude aldehyde as a light green oil: NMR δ 9.80 (br s, 1H), 7.40 (m, 5H), 5.55 (br s, 1H), 5.20 (m, 3H), 4.38 (t, J=6.0 Hz, 1H), 2.6-2.1 (m, 4H).

Workup

  1. addition13 mL (10.7 g, 141 mmol) of borane-methyl sulfide complex is added dropwise via an addition funnel
  2. concentrationThe resulting mixture is concentrated in vacuo
  3. customto give a white glassy material which
  4. temperatureto warm to room temperature
  5. stirringstirred for 3 h
  6. filtrationThe mixture is filtered through diatomaceous earth with ether (200 mL)
  7. concentrationthen concentrated
  8. filtrationfiltered again through diatomaceous earth with ether
  9. concentrationthen concentrated

Sources & evidence

ORD record
ord-2df57cb02bc347c793c03c88f8cf9690
Source dataset
uspto-grants-1996_08
Patent number
US05545662

Reaction notes

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