1,4-Dioxane hydrochloride → HCID 17984379, compound

HRID 1181069Notes

Reaction equation

HRID 1181069 reaction equation
C([O:5][C:6](=[O:45])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:37][NH:38][C:39]([O:41][CH:42]([CH3:44])[CH3:43])=[O:40])(C)(C)C.Cl.O1CCOCC1>>[CH:42]([O:41][C:39]([NH:38][CH2:37][C:10]1[CH:11]=[C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[CH:26][C:27]([O:30][CH:31]4[CH2:32][CH2:33][O:34][CH2:35][CH2:36]4)=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])[CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][C:6]([OH:45])=[O:5])=[O:40])([CH3:44])[CH3:43]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69233523HCID 69233523, compound

Product 1

HCID 17984379HCID 17984379, compound

Procedure

A mixture of 3-[4-{2-[2-(4-hydroxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester (120 mg, 0.223 mmol, Example 406), tetrahydro-pyran-4-ol (22.7 mg, 0.223 mmol), triphenylphosphine (58.4 mg, 0.223 mmol) and toluene (10 mL) was treated dropwise with DIAD (45 mg, 0.223 mmol). The mixture was stirred under N2 at ambient temperature for 16 h and concentrated. The crude product was purified by radial chromatography (10-70% EtOAc/hexanes) to give 3-[2-(isopropoxycarbonylamino-methyl)-4-(2-{5-methyl-2-[4-(tetrahydro-pyran-4-yloxy)-phenyl]-oxazol-4-yl}-ethoxy)-phenyl]-propionic acid tert-butyl ester. The ester product was dissolved 4M HCl/dioxane (5 mL), stirred for 16 h and concentrated to give the title compound: MS [ES] m/z 525 (M+H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-95deab51f962407a9a29db3689f0adfc
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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