Ammonia → Methanesulfonic acid 4-[(RS)-2-amino-4-(3-bromo-phenyl)-4,5-dihydro-oxazol-4-yl]-phenyl ester

HRID 1668731Notes

Reaction equation

HRID 1668731 reaction equation
II.[Br:3][C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][CH:13]=2)=[CH2:11])[CH:7]=[CH:8][CH:9]=1.[NH3:23].C([O:27][CH2:28]C)(=O)C.C(#[N:32])C>C(OCC)(=O)C.[Ag]OC#N>[NH2:23][C:28]1[O:27][CH2:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][CH:13]=2)([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([Br:3])[CH:5]=2)[N:32]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 807IodineHCID 21930812Acetonitrile ethyl acetateHCID 57825215Methanesulfonic acid 4-[1-(3-bromo-phenyl)-vinyl]-phenyl ester

Product 1

HCID 57825000Methanesulfonic acid 4-[(RS)-2-amino-4-(3-bromo-phenyl)-4,5-dihydro-oxazol-4-yl]-phenyl esterYield 35%

Reagents, catalysts & solvents 2

HCID 178513473HCID 178513473, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

According to general method 2, a solution of iodine in ethyl acetate was added to a mixture of methanesulfonic acid 4-[1-(3-bromo-phenyl)-vinyl]-phenyl ester (1600 mg, 4.53 mmol) and silver cyanate (1.1 eq) in ethyl acetate/acetonitrile. The crude product of this reaction was subsequently reacted with aqueous ammonia (30% by vol). Purification by SCX followed by silica column (dichloromethane/methanol, 95:5) yielded 480 mg of product (35%).

Workup

  1. customPurification by SCX

Sources & evidence

ORD record
ord-47e0306060ab48de839f0938725300d6
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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