Tetrahydrofuran → HCID 131733514, compound

HRID 2281106Notes

Reaction equation

HRID 2281106 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[OH:20])=[N:7][CH:8]=[N:9]2)=[C:4]([F:21])[CH:3]=1.[CH2:22]([O:24][C:25](=[O:29])[C@@H:26](O)[CH3:27])[CH3:23].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[O:20][C@H:26]([CH3:27])[C:25]([O:24][CH2:22][CH3:23])=[O:29])=[N:7][CH:8]=[N:9]2)=[C:4]([F:21])[CH:3]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 92831(L)-ethyl lactateHCID 117772878HCID 117772878, compound

Product 1

HCID 131733514HCID 131733514, compound

Procedure

To a mixture of 28 g (79.5 mmol) 2-[(7-bromo-5-fluoro-quinazolin-4-yl)amino]-5-fluoro-phenol, 9.4 g (79.5 mmol) (S)-2-Hydroxy-propionic acid ethyl ester, 25.1 g (95.6 mmol) PPh3 and THF 22 g (95.4 mmol) di-tert-butyl azodicarboxylate are added and the mixture stirred over night. The solvent is evaporated and isopropanol is added, the precipitate is filtered off and dried furnishing ethyl (2R)-2-[2-[(7-bromo-5-fluoro-quinazolin-4-yl)amino]-5-fluoro-phenoxy]propanoate.

Workup

  1. additionare added
  2. customThe solvent is evaporated
  3. additionisopropanol is added
  4. filtrationthe precipitate is filtered off
  5. customdried

Sources & evidence

ORD record
ord-1d4604f9379b462d9a417246c83b0d69
Source dataset
uspto-grants-2015_09
Patent number
US09139577B2

Reaction notes

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