Triphenylphosphine → HCID 178501381, compound

HRID 1352517Notes

Reaction equation

HRID 1352517 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][OH:8])=[C:5]([CH3:9])[O:4][N:3]=1.[O:10]=[S:11]1(=[O:34])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]([NH:20][C@@H:21]([CH2:26][C:27]2[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=2)[C:22]([O:24][CH3:25])=[O:23])=[N:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[O:10]=[S:11]1(=[O:34])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]([NH:20][C@@H:21]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:8][CH2:7][C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:9])=[CH:29][CH:28]=2)[C:22]([O:24][CH3:25])=[O:23])=[N:12]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2895753,5-Dimethyl-4-(hydroxymethyl)isoxazoleHCID 5462977Diethyl azodicarboxylateHCID 178501373HCID 178501373, compound

Product 1

HCID 178501381HCID 178501381, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

(3,5-Dimethylisoxazol-4-yl)methanol (0.28 g, 1.5 mmol), methyl (2S)-2-[(1,1-dioxo-1,2-benzoisothiazol-3-yl)amino]-3-(4-hydroxyphenyl)propionate (0.36 g, 1 mmol) and triphenylphosphine (0.79 g, 3 mmol) were dissolved in tetrahydrofuran (2 ml). After cooling to 5° C., DEAD (0.52 g, 3 mmol) was added to the reaction mixture. The reaction was then stirred at room temperature for 18–24 h. THF was evaporated to obtain crude title product.

Workup

  1. customTHF was evaporated

Sources & evidence

ORD record
ord-a17195e243cc4d33be3e4516f81a5079
Source dataset
uspto-grants-2007_05
Patent number
US07220766B2

Reaction notes

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