Triphenylphosphine → HCID 178527243, compound

HRID 277138Notes

Reaction equation

HRID 277138 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][SH:11](=[O:13])=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH:45]([N:58]1[CH2:61][CH:60](O)[CH2:59]1)([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>O1CCCC1>[CH:45]([N:58]1[CH2:61][CH:60]([N:10]([CH2:9][C:4]2[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=2)[SH:11](=[O:13])=[O:12])[CH2:59]1)([C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 178527241HCID 178527241, compound

Product 1

HCID 178527243HCID 178527243, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(1-Benzhydrylazetidin-3-yl)-N-(3,5-difluorophenyl)methylsulfonamide may be obtained by carrying out the procedure as in Example 13 (method 2) in the following manner: 0.86 g of N-(3,5-difluorophenyl)methylsulfonamide, 3.28 g of triphenylphosphine and then 2 ml of diethyl azodicarboxylate are added successively to a solution of 2 g of 1-benzhydrylazetidin-3-ol in 100 cm3 of tetrahydrofuran. An increase in the temperature, which passes from 22° C. to 29° C., as well as the formation of a precipitate immediately following the addition of the diethyl azodicarboxylate are observed. After 20 h at 22° C., the precipitate is removed by filtration and the filtrate is concentrated to dryness at 40° C. under 2.7 kPa. The residue is triturated with 5 cm3 of methanol for 20 minutes at 21° C., providing 1.07 g of N-(1-benzhydrylazetidin-3-yl)-N-(3,5-difluorophenyl)methylsulfonamide in the form of a white amorphous solid.

Workup

  1. temperatureAn increase in the temperature, which
  2. custompasses from 22° C. to 29° C.
  3. customthe precipitate is removed by filtration
  4. concentrationthe filtrate is concentrated to dryness at 40° C. under 2.7 kPa
  5. customThe residue is triturated with 5 cm3 of methanol for 20 minutes at 21° C.

Sources & evidence

ORD record
ord-192c5758d604445882cf7bbf5168cb17
Source dataset
uspto-grants-2002_03
Patent number
US06355631B1

Reaction notes

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