Water → N-(4,5-Difluoro-6-(2-fluoro-4-iodophenylamino)benzo[d]oxazol-7-yl)-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide

HRID 1914906Notes

Reaction equation

HRID 1914906 reaction equation
[F:1][C:2]1C2N=COC=2[C:5]([NH:11][S:12]([C:15]2([CH2:18]C=C)[CH2:17][CH2:16]2)(=[O:14])=[O:13])=[C:4]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])[C:3]=1[F:30].C[N+:32]1([O-])[CH2:37][CH2:36][O:35][CH2:34]C1.[OH2:39].[CH2:40]1[CH2:44][O:43]CC1>[Os](=O)(=O)(=O)=O>[F:1][C:2]1[C:37]2[N:32]=[CH:34][O:35][C:36]=2[C:5]([NH:11][S:12]([C:15]2([CH2:18][CH:40]([OH:39])[CH2:44][OH:43])[CH2:17][CH2:16]2)(=[O:13])=[O:14])=[C:4]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])[C:3]=1[F:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 532415631-Allyl-cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)-benzooxazol-7-yl]-amide

Product 1

HCID 53241564N-(4,5-Difluoro-6-(2-fluoro-4-iodophenylamino)benzo[d]oxazol-7-yl)-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamideYield 26.9%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

Following the procedure set forth in Example 1I, 1-allyl-cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)benzoxazol-7-yl]-amide (7 g, 0.0127 mol) in THF (150 mL) was reacted with N-methyl morpholine-N-oxide (2.23 g, 0.019 mol), osmium tetroxide (0.32 g, 0.00127 mol) and water (15 mL) to afford the crude product. Purification by column chromatography on silica gel (0-2.5% methanol in DCM), followed by separation of the optical isomers using chiral HPLC afforded 1 g of the product

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (0-2.5% methanol in DCM)
  3. customfollowed by separation of the optical isomers

Sources & evidence

ORD record
ord-cf342e304584415f88af44532fc5a275
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

Loading…