Dimethylformamide dimethyl acetal → HCID 178472051, compound

HRID 1904594Notes

Reaction equation

HRID 1904594 reaction equation
[Br:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[C:5]([C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[C:4]([F:18])[C:3]=1[F:19].[CH3:20]N(C(OC)OC)C.[NH2:28][C@@H:29]([CH3:32])[CH2:30][OH:31]>O1CCCC1>[Br:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[C:5]([C:6]([C:8](=[CH:20][NH:28][C@@H:29]([CH3:32])[CH2:30][OH:31])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[C:4]([F:18])[C:3]=1[F:19]

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 80307L-AlaninolHCID 9974705Ethyl 3-(4-bromo-2,3,5,6-tetrafluorophenyl)-3-oxopropanoate

Product 1

HCID 178472051HCID 178472051, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 19.99 g ethyl 4-bromo-2,3,5,6-tetrafluorobenzoylacetate and 7.8 ml DMF dimethyl acetal in 60 ml tetrahydrofuran was stirred at room temperature for about 16 hours. The mixture was then cooled in an ice-bath and 4.6 ml (S)-2-amino-1-propanol was added. The resulting clear solution was concentrated in vacuo, and the residue was dissolved in ether and chromatographed on a column of silica gel using ether as eluant. There was obtained 22.4 g of ethyl (S)-2-(4-bromo-2,3,5,6-tetrafluorobenzoyl)-N-(1-hydroxy-2-propyl)-3-aminopropenoate as a light yellow solid, m.p. 127°-134° C., [α]D25 =+17.6°.

Workup

  1. temperatureThe mixture was then cooled in an ice-bath
  2. concentrationThe resulting clear solution was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ether
  4. customchromatographed on a column of silica gel

Sources & evidence

ORD record
ord-d7ea9ca7708145efbd5b391339f74a95
Source dataset
uspto-grants-1989_06
Patent number
US04839355

Reaction notes

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