Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate → HCID 71622139, compound

HRID 926160Notes

Reaction equation

HRID 926160 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:30])[C:8]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22]CC)=[O:21])=[C:9]2[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[CH3:31][C:32]1[S:33][C:34]([C:38]([OH:42])([C:40]#[CH:41])[CH3:39])=[C:35]([CH3:37])[N:36]=1>>[C:26]([O:25][C@@H:19]([C:8]1[C:7]([CH3:30])=[CH:6][C:5]2[C:10](=[CH:11][C:2]([C:41]#[C:40][C:38]([C:34]3[S:33][C:32]([CH3:31])=[N:36][C:35]=3[CH3:37])([OH:42])[CH3:39])=[CH:3][CH:4]=2)[C:9]=1[C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[C:20]([OH:22])=[O:21])([CH3:27])([CH3:28])[CH3:29]

Participants

3

Reactant 2

HCID 67126201Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetateHCID 87266638HCID 87266638, compound

Product 1

HCID 71622139HCID 71622139, compound

Procedure

(2S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-7-(3-(2,4-dimethylthiazol-5-yl)-3-hydroxybut-1-ynyl)-3-methylnaphthalen-2-yl)acetic acid was prepared by the method in Example 8 from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate and 2-(2,4-dimethylthiazol-5-yl)but-3-yn-2-ol. 1H-NMR: 400 MHz, (CD3OD) δ: 7.78 (d, J=8 Hz, 1H), 7.70 (s, 1H), 7.58 (m, 3H), 7.43 (d, J=8 Hz, 1H), 7.32 (m, 2H), 5.18 (s, 1H), 2.64 (s, 3H), 2.61 (s, 3H), 2.47 (s, 3H), 1.82 (s, 3H), 0.98 (s, 9H). LCMS-ESI+ (m/z): [M+H]+ calcd for C32H32ClNSO4: 562.2. found: 562.1.

Sources & evidence

ORD record
ord-a54d433b01b0403e85488ebb3ad3e161
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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