Triphenylphosphine → HCID 86731242, compound

HRID 2277184Notes

Reaction equation

HRID 2277184 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:13][C:14]4[C:20]([F:21])=[C:19]([OH:22])[CH:18]=[CH:17][C:15]=4[N:16]=3)=[C:8]([F:23])[C:7]=2[F:24])[CH2:3][CH2:2]1.O[CH2:26][C@@H:27]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH3:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:13][C:14]4[C:20]([F:21])=[C:19]([O:22][CH2:28][C@@H:27]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])[CH3:26])[CH:18]=[CH:17][C:15]=4[N:16]=3)=[C:8]([F:23])[C:7]=2[F:24])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 66880968DIAD tolueneHCID 86731240HCID 86731240, compound

Product 1

HCID 86731242HCID 86731242, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(cyclopropylmethoxy)-2,3-difluorophenyl)-7-fluoro-1,3-benzoxazol-6-ol (1.37 g), tert-butyl ((2S)-1-hydroxypropan-2-yl)carbamate (1.07 g) and triphenylphosphine (1.61 g) in THF (15 mL) was added dropwise diisopropyl azodicarboxylate toluene solution (1.9 M, 3.23 mL) at 0° C., and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (1.18 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dc1104d61f3047e3bbd16bca19047ae2
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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