Ammonia → 3-Amino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid tert-butyl ester

HRID 1245395Notes

Reaction equation

HRID 1245395 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH:7]=[CH:8][CH:9]1[O:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[C:24]([CH3:32])[CH:23]=3)=[CH:16][CH:15]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[NH3:34]>CO>[C:1]([O:5][C:6](=[O:33])[CH2:7][CH:8]([NH2:34])[CH:9]1[O:13][N:12]=[C:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[C:24]([CH3:32])[CH:23]=3)=[CH:18][CH:19]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 696396783-{3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acrylic acid tert-butyl ester

Product 1

HCID 696401513-Amino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid tert-butyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The product from step 10c (0.3 g, 0.67 mmol) was dissolved in methanol (10 mL) and condensed ammonia (10 mL) in a stainless steel pressure reactor and heated to 60° C. for 5 h. The reaction was complete and was concentrated to give 3-amino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid tert-butyl ester (0.3 g, 97%) as an oil. MS found: (M+H)+=462.

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-e1d152ffdbe541c0a18077ab39583f77
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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