Triphenylphosphine → HCID 53860470, compound

HRID 2070182Notes

Reaction equation

[N:1]([C@H:4]1[C@H:19](O)[CH2:18][C@@H:17](/C(/C)=C/C2N=C(C)SC=2)[O:16][C:15](=[O:30])[CH2:14][C@H:13](O)[C:12](C)(C)[C:11](=[O:34])[C@H:10](C)[C@@H:9](O)[C@@H:8](C)[CH2:7][CH2:6][CH2:5]1)=[N+]=[N-].N([C@H]1C[C@@H](/C(/C)=C/C2N=C(C)SC=2)OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC[C@@H]1O)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[CH:19]12[NH:1][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:34])[CH2:12][CH2:13][CH2:14][C:15](=[O:30])[O:16][CH2:17][CH2:18]2

Participants

Conditions

Temperature: 30 °C

Procedure

To a stirred solution of (4S,7R,8S,9S,13R,14R,16S)-13-Azido-4,8,14-trihydroxy-5,5,7,9-tetramethyl-16-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)oxacyclohexadecane-2,6-dione and (4S,7R,8S,9S,13S,14S,16S)-14-Azido-4,8,13-trihydroxy-5,5,7,9-tetramethyl-16-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)oxacyclohexadecane-2,6-dione mixture (12.8 g, 23.85 mmol) in anhydrous acetonitrile (90 mL) was added triphenylphosphine (9.48 g, 35.77 mmol) under nitrogen atmosphere. The clear solution was stirred at 20-40° C. for 19-40 h. The reaction mixture was cooled to 0-5° C. for 3-4 h and filtered the product. The cake was washed with heptane (64 mL) and dried at 40° C. under reduced pressure for 15-18 h to give (1S,3S,7S,10R,11S,12S16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-34(E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4-oxa-17-azabicyclo(14.1.0)heptadecane-5,9-dione as a white solid (5.41 g, 46%).

Workup

temperatureThe reaction mixture was cooled to 0-5° C. for 3-4 h
filtrationfiltered the product
washThe cake was washed with heptane (64 mL)
customdried at 40° C. under reduced pressure for 15-18 h

Sources & evidence

ORD record: ord-7e3d12c1a6fe4614ab805b64a3e5715e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299266B2

Reaction notes

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