Triphenylphosphine → (S)-Methyl 2-(N-(3-methylenehexyl)-2-nitrophenylsulfonamido)pent-4-enoate

HRID 253016Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C@@H:14]([CH2:19][CH:20]=[CH2:21])[C:15]([O:17][CH3:18])=[O:16])(=[O:12])=[O:11])([O-:3])=[O:2].[CH2:22]=[C:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:22]=[C:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][N:13]([C@@H:14]([CH2:19][CH:20]=[CH2:21])[C:15]([O:17][CH3:18])=[O:16])[S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

Tetrahydrofuran (30.2 ml) was added to 2.27 g (7.22 mmol) of the title compound produced in step (i) of Example 47 and 1.07 g (9.39 mmol) of the title compound produced in step (ii) of Example 47. The mixture was cooled to 0° C., 2.84 g (10.8 mmol) of triphenylphosphine was added thereto, and the mixture was stirred for 10 min. Diisopropyl azodicarboxylate (2.1 ml, 10.8 mmol) was added thereto. The temperature of the mixture was raised over a period of 2 hr before it was stirred for 19 hr. The solvent was removed under the reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1) to give 2.42 g (yield 82%) of the title compound.

Workup

temperatureThe temperature of the mixture was raised over a period of 2 hr before it
stirringwas stirred for 19 hr
customThe solvent was removed under the reduced pressure
customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record: ord-ceebbbc641ee45af8ba34a9baafeb71d
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07871982B2

Reaction notes

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