Trifluoroacetic acid → Phenylmethyl 2-((3S,1R)-3-{[5-methyl-3-(6-fluoro-2-iodophenyl)isoxazol-4-yl]carbonylamino}cyclohexyl)acetate

HRID 352170Notes

Reaction equation

HRID 352170 reaction equation
[C:1]([OH:7])([C:3](F)(F)F)=[O:2].[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([I:15])[C:10]=1[C:16]1[C:20]([C:21]([OH:23])=O)=[C:19]([CH3:24])[O:18][N:17]=1.CC[N:27]([CH2:30][CH3:31])CC>ClCCl>[CH3:24][C:19]1[O:18][N:17]=[C:16]([C:10]2[C:9]([F:8])=[CH:14][CH:13]=[CH:12][C:11]=2[I:15])[C:20]=1[C:21]([NH:27][C@H:30]1[CH2:31][CH2:24][CH2:19][C@@H:20]([CH2:3][C:1]([O:7][CH2:16][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:9]=2)=[O:2])[CH2:21]1)=[O:23]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 179306454-Carboxy-5-methyl-3-(2-iodo-6-fluoro-phenyl)isoxazole

Product 1

HCID 69848288Phenylmethyl 2-((3S,1R)-3-{[5-methyl-3-(6-fluoro-2-iodophenyl)isoxazol-4-yl]carbonylamino}cyclohexyl)acetateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a fashion similar to that described for preparation 99, a compound from preparation 45 (5.1 g, 14.7 mmol), dichloromethane (30 mL), TFA (30 mL), dichloromethane (150 mL), 3-(2-fluoro-6-iodo-phenyl)-5-methylisoxazole-4-carboxylic acid (6.39 g, 17.49 mmol), and Et3N (6.03 mL, 43.4 mmol) gave the title compound (7.15 g, 86%) after column chromatography (silica gel, hexanes/EtOAc gradient). Mass Spectrum (ES+) (m/z) 577.0 [M+1].

Workup

  1. customIn a fashion similar to that described for preparation 99

Sources & evidence

ORD record
ord-e0baba97c244494b9fbd431ca8c64902
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

Loading…