Triphenylphosphine → HCID 131729366, compound

HRID 420277Notes

Reaction equation

[NH2:1][C:2]1[C:31]([CH:32]=C)=[CH:30][C:5]([CH2:6][C@H:7]2[C@H:15]3[C@@H:11]([N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:19]=4)[C:13](=[O:16])[O:14]3)[CH2:10][S:9](=[O:29])(=[O:28])[CH2:8]2)=[CH:4][C:3]=1[F:34].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.C[OH:58]>>[NH2:1][C:2]1[C:3]([F:34])=[CH:4][C:5]([CH2:6][C@H:7]2[C@H:15]3[C@@H:11]([N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:26])([CH3:25])[CH3:27])[CH:19]=4)[C:13](=[O:16])[O:14]3)[CH2:10][S:9](=[O:29])(=[O:28])[CH2:8]2)=[CH:30][C:31]=1[CH:32]=[O:58]

Participants

Reactant 3

HCID 11776Triphenylphosphine

HCID 21226129Dichloromethane methanol

HCID 66649728HCID 66649728, compound

Product 1

HCID 131729366HCID 131729366, compound

Conditions

Temperature: 25 °C

Procedure

A solution of (3aR*,7S*,7aS*)-7-(4-amino-3-fluoro-5-vinyl-benzyl)-3-(3-tert-butyl-benzyl)-5,5-dioxo-hexahydro-1-oxa-5lambda*6*-thia-3-aza-inden-2-one (0.215 g, 0.44 mmol) in CH2Cl2-MeOH 4:1 (10 mL) was ozonized at −78° C. until the educt disappeared. After addition of PPh3 (0.139 g, 0.53 mmol) the reaction mixture was allowed to warm to 25° C. and the solvents were removed under reduced pressure. The title compound was obtained after flash-chromatography on silica gel (hexane-EtOAc 2:1) as white solid: ESIMS [M−H]−=487.

Workup

customwas ozonized at −78° C. until the educt
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-8a263ad329ed46f4b73c026d3ba94df4
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093406B2

Reaction notes

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