2-Bromoethanol → HCID 71597740, compound

HRID 405103Notes

Reaction equation

[N:1]1([CH2:4][C@:5]23[CH2:39][CH2:38][C@@H:37]([C:40]([CH3:42])=[CH2:41])[C@@H:6]2[C@@H:7]2[C@@:20]([CH3:23])([CH2:21][CH2:22]3)[C@@:19]3([CH3:24])[C@@H:10]([C@:11]4([CH3:36])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:26])([CH3:25])[C:14]([C:27]3[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8]2)CC1.Br[CH2:44][CH2:45][OH:46]>>[OH:46][CH2:45][CH2:44][NH:1][CH2:4][C@:5]12[CH2:39][CH2:38][C@@H:37]([C:40]([CH3:42])=[CH2:41])[C@@H:6]1[C@@H:7]1[C@@:20]([CH3:23])([CH2:21][CH2:22]2)[C@@:19]2([CH3:24])[C@@H:10]([C@:11]3([CH3:36])[C@@H:16]([CH2:17][CH2:18]2)[C:15]([CH3:26])([CH3:25])[C:14]([C:27]2[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1

Participants

Reactant 2

HCID 108982-Bromoethanol

HCID 71597654HCID 71597654, compound

Product 1

HCID 71597740HCID 71597740, compound

Procedure

The title compound was prepared following the general procedures described above for the synthesis of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(aziridin-1-ylmethyl)-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)benzoic acid using 2-bromoethanol as the alkylating reagent in step 1. The product was isolated as a white solid (21.9 mg, 79.9%). LCMS: m/e 588.9 (MH+), 2.373 min (method 9). 1H NMR (500 MHz, DMSO-d6) δ 7.88 (d, J=8.2 Hz, 2H), 7.23 (d, J=8.2 Hz, 2H), 5.25 (d, J=4.9 Hz, 1H), 4.72 (s, 1H), 4.61 (s, 1H), 3.74 (m, 2H), 3.14 (br. s., 1H), 3.08 (m, 2H), 2.80-2.68 (m, 1H), 2.45 (m, 1H), 2.12-1.94 (m, 2H), 1.93-1.79 (m, 2H), 1.74-1.58 (m, 8H), 1.57-1.29 (m, 8H), 1.28-1.13 (m, 4H), 1.08 (s, 4H) 1.00 (3H, s), 0.96 (3H, s), 0.91 (6H, s).

Sources & evidence

ORD record: ord-f6cbf0e2a87044c087e7ced63072687f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748415B2

Reaction notes

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