L-Alanine 1,1-dimethylethyl ester → HCID 56599779, compound

HRID 572597Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]([CH:25](O)[CH3:26])[CH:22]=[CH:23][CH:24]=3)[N:15]=2)=[CH:10][C:9]=1[C:28]([F:31])([F:30])[F:29].[NH2:32][C@@H:33]([CH3:41])[C:34]([O:36]C(C)(C)C)=[O:35]>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=3)[CH2:25][CH2:26][NH:32][C@@H:33]([CH3:41])[C:34]([OH:36])=[O:35])[N:15]=2)=[CH:10][C:9]=1[C:28]([F:31])([F:30])[F:29]

Participants

Reactant 2

HCID 89016L-Alanine 1,1-dimethylethyl ester

HCID 66652673HCID 66652673, compound

Product 1

HCID 56599779HCID 56599779, compound

Procedure

The title compound was prepared following the protocol used for Example 91, Steps 2 and 3, but starting from (3-(5-(2′-methyl-2-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethanol (84 mg, 0.2 mmol) and (S)-tert-butyl 2-aminopropanoate (87 mg, 0.6 mmol). It was isolated as a white solid (133 mg, 96%). 1H NMR: (DMSO-d6, 400 MHz) δ 8.57 (s, 1H), 8.53 (d, J=8.1 Hz, 1H), 8.07-8.03 (m, 2H), 7.69 (d, J=8.0 Hz, 1H), 7.65-7.53 (m, 2H), 7.44-7.37 (m, 2H), 7.33 (td, J=4.0, 2.1 Hz, 1H), 7.20 (d, J=7.6 Hz, 1H), 3.31 (q, J=7.2 Hz, 2H), 3.18-3.02 (m, 3H), 2.06 (s, 3H), 1.33 (d, J=7.0 Hz, 3H). LC/MS (Method B): 496 (M+H)+. HPLC (Method G) Rt 3.24 min (Purity: 99.1%).

Sources & evidence

ORD record: ord-72eaae421b4a4ab5942d959fef7e097f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029405B2

Reaction notes

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