tert-Butyl bromoacetate → HCID 66653116, compound

HRID 572587Notes

Reaction equation

HRID 572587 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]([NH2:22])[CH3:21])=[CH:16][CH:15]=3)[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([F:32])([F:31])[F:30].Br[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>>[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([CH:20]([NH:22][CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH3:21])=[CH:18][CH:19]=3)[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([F:32])([F:31])[F:30].[ClH:1].[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([CH:20]([NH:22][CH2:34][C:35]([OH:37])=[O:36])[CH3:21])=[CH:18][CH:19]=3)[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([F:32])([F:31])[F:30]

Participants

4

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 131732827HCID 131732827, compound

Product 2

HCID 66653116HCID 66653116, compoundHCID 131732826HCID 131732826, compound

Procedure

Tert-butyl N-[1-(4-{5-[2-methyl-2′-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]glycinate was prepared following the general procedure 11 starting from 1-(4-{5-[2-methyl-2′-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethanamine, hydrochloride salt and tert-butyl bromoacetate. It was hydrolyzed following general procedure 8, affording the title compound as a white powder. 1H NMR: (DMSO-d6, 300 MHz) δ 8.18 (m, 3H), 8.08 (m, 1H), 7.91 (d, J=7.90 Hz, 1H), 7.77 (m, 3H), 7.69 (m, 1H), 7.41 (m, 2H), 4.74 (m, 1H), 3.74 (m, 1H), 3.52 (m, 1H), 2.11 (s, 3H), 1.61 (d, J=6.8 Hz, 3H). LC/MS (Method B): 482.2 (M+H)+, 480.2 (M−H)−. HPLC (Method A) Rt 4.25 min (Purity: 99.9%).

Sources & evidence

ORD record
ord-cc643ade2fdd4f94a354f0a16bdac2bb
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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