5-(Methoxycarbonyl)thiophene-2-boronic acid → HCID 86676631, compound

HRID 85702Notes

Reaction equation

HRID 85702 reaction equation
[NH2:1][C@:2]12[CH2:37][CH2:36][C@@H:35]([C:38]([CH3:40])=[CH2:39])[C@@H:3]1[C@@H:4]1[C@@:17]([CH3:20])([CH2:18][CH2:19]2)[C@@:16]2([CH3:21])[C@@H:7]([C@:8]3([CH3:34])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:23])([CH3:22])[C:11]([C:24]2C=C[C:27]([C:28]([OH:30])=[O:29])=[C:26](F)[CH:25]=2)=[CH:10][CH2:9]3)[CH2:6][CH2:5]1.COC(C1[S:49]C(B(O)O)=CC=1)=O>>[NH2:1][C@:2]12[CH2:37][CH2:36][C@@H:35]([C:38]([CH3:40])=[CH2:39])[C@@H:3]1[C@@H:4]1[C@@:17]([CH3:20])([CH2:18][CH2:19]2)[C@@:16]2([CH3:21])[C@@H:7]([C@:8]3([CH3:34])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:23])([CH3:22])[C:11]([C:24]2[S:49][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=2)=[CH:10][CH2:9]3)[CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 116007975-(Methoxycarbonyl)thiophene-2-boronic acidHCID 601522384-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)-2-fluorobenzoic acid

Product 1

HCID 86676631HCID 86676631, compound

Procedure

The title compound was prepared following the method described above for the synthesis of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)-2-fluorobenzoic acid using 5-(methoxycarbonyl)thiophen-2-ylboronic acid as the coupling reagent in Step 1. The product was isolated as a white solid (2.7 mg, 44%). LCMS: m/e 536.30 (M+H)+, 2.25 min (method 10). 1H NMR (500 MHz, Acetic) δ 7.77 (d, J=4.0 Hz, 1H), 6.98 (d, J=3.7 Hz, 1H), 5.87 (d, J=4.3 Hz, 1H), 4.88 (s, 1H), 4.75 (s, 1H), 2.79 (td, J=10.5, 6.7 Hz, 1H), 2.35-2.13 (m, 4H), 1.98-1.85 (m, 4H), 1.83-1.07 (m, 14H), 1.77 (s, 3H), 1.19 (s, 3H), 1.14 (s, 3H), 1.14 (s, 3H), 1.10 (s, 3H), 1.02 (s, 3H).

Sources & evidence

ORD record
ord-99cd5c693c98413fa9f939399cab95de
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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