Triphenylphosphine → HCID 11539237, compound

HRID 1176717Notes

Reaction equation

O[C@H:2]1[CH2:7][C@@H:6]([CH3:8])[S:5](=[O:10])(=[O:9])[C:4]2[S:11][CH:12]=[CH:13][C:3]1=2.[CH2:14]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>C(Cl)Cl>[CH2:14]([N:16]([C@H:2]1[CH2:7][C@H:6]([CH3:8])[S:5](=[O:10])(=[O:9])[C:4]2[S:11][CH:12]=[CH:13][C:3]1=2)[S:17]([C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1)(=[O:18])=[O:19])[CH3:15]

Participants

Conditions

Temperature: -20 °C

Procedure

Methylene chloride (60 mL), cis-4-hydroxy-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran-7,7-dioxide (5 g), N-ethyl-4-nitrobenzene-sulfonamide (6.86 g) and triphenyl-phosphine (8.42 g) are mixed under nitrogen atmosphere. The mixture is cooled to under −20° C. and diisopropyl azadicarboxylate (5.9 mL) is added, maintaining the temperature under −20° C. The temperature is allowed to rise to 20-25° C. The obtained mixture is treated with 5% NaOH (125 mL) and the resulting organic phase is vacuum distilled to dryness. The residue is chromatographed in a column (ethyl acetate/heptane, 2/1), obtaining 4.97 g of trans-4-[N-ethyl-N-(4-nitrobenzenesulfonyl)amino]-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran-7,7-dioxide.

Workup

additionis added
temperaturemaintaining the temperature under −20° C
customto rise to 20-25° C
distillationdistilled to dryness
customThe residue is chromatographed in a column (ethyl acetate/heptane, 2/1)

Sources & evidence

ORD record: ord-4d200f30753241b8a8b2e083ffe991e8
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842821B2

Reaction notes

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