Methanol → 8-[1-(2,3-Dihydroxy-propyl)-cyclopropanesulfonylamino]-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester

HRID 1259377Notes

Reaction equation

HRID 1259377 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[C:13]([NH:28][S:29](C3(CC=C)CC3)(=[O:31])=[O:30])[C:14]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=3[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:42][CH2:41]C1.[CH3:46]O.[CH2:48]1[CH2:52][O:51][CH2:50][CH2:49]1>O.C(Cl)(Cl)Cl.O=[Os](=O)(=O)=O>[C:1]([O:5][C:6]([N:8]1[C:12]2=[C:13]([NH:28][S:29]([C:49]3([CH2:48][CH:52]([OH:51])[CH2:41][OH:42])[CH2:46][CH2:50]3)(=[O:31])=[O:30])[C:14]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=3[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 673454828-(1-Allyl-cyclopropanesulfonylamino)-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 671938308-[1-(2,3-Dihydroxy-propyl)-cyclopropanesulfonylamino]-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

OsO4 (0.004 g, 0.00002 mol) was added to a stirred solution of 8-(1-allyl-cyclopropanesulfonylamino)-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester (125 mg, 0.0002 mol) and N-methylmorpholine-N-oxide (34 mg, 0.0003 mol) in water and THF (3 mL). The resulting mixture was stirred at room temperature for 3 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ethylacetate and water. The organic layer concentrated to afford 80 mg of the crude product which was used in the next step without further purification.

Workup

  1. customThe reaction mixture was partitioned between ethylacetate and water
  2. concentrationThe organic layer concentrated

Sources & evidence

ORD record
ord-75cc4fdf6d7f44ca98abb531cfeca682
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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