Triphenylphosphine → HCID 11669858, compound

HRID 970085Notes

Reaction equation

[CH3:1][C:2]1[C:6]([CH2:7][OH:8])=[C:5]([CH3:9])[O:4][N:3]=1.O[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]([NH:23][C:24]2[S:25][CH:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:28]=2)[C:19]([O:21][CH3:22])=[O:20])=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][C@H:18]([NH:23][C:24]3[S:25][CH:26]=[C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:28]=3)[C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:16]=2)=[C:5]([CH3:9])[O:4][N:3]=1

Participants

Conditions

Temperature: 5 °C

Procedure

(3,5-Dimethylisoxazol-4-yl)methanol (0.28 g, 1.5 mmol), methyl(2S)-3-(4-hydroxyphenyl)-2-[(4-phenyl-1,3-thiazol-2-yl)amino]propionate from Step A (0.35 g, 1 mmol) and triphenylphosphine (0.79 g, 3 mmol) were dissolved in tetrahydrofuran (THF). After cooling the reaction mixture to 5° C., DEAD (0.52 g, 3 mmol) was added. The reaction was then stirred at room temperature for 18–24 h. THF was evaporated to obtain crude methyl(2S)-3-{4-[(3,5-dimethylisoxazol-4-yl)methoxy]phenyl}-2-[(4-phenyl-1,3-thiazol-2-yl)amino]propionate.

Workup

customTHF was evaporated

Sources & evidence

ORD record: ord-09534abbdec34960ae9fc2d271f7f548
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07309791B2

Reaction notes

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