Potassium Bromide → HCID 11453970, compound

HRID 1677839Notes

Reaction equation

HRID 1677839 reaction equation
[K+].[Br-].[CH3:3][C@@H:4]1[C:33]([CH3:35])([CH3:34])[O:32][C@:6]2([O:10][C@H:9]3[CH2:11][C@H:12]4[C@@H:18]5[CH2:19][CH2:20][C@H:21]6[CH2:26][C@H:25]([OH:27])[CH2:24][CH2:23][C@:22]6([CH3:28])[C@H:17]5[C:15](=[O:16])[CH2:14][C@:13]4([CH3:29])[C@H:8]3[C@:7]2([OH:31])[CH3:30])[CH2:5]1>C(Cl)(Cl)Cl>[CH3:3][C@@H:4]1[C:33]([CH3:34])([CH3:35])[O:32][C@@:6]2([O:10][C@H:9]3[CH2:11][C@H:12]4[C@@H:18]5[CH2:19][CH2:20][C@H:21]6[CH2:26][C@H:25]([OH:27])[CH2:24][CH2:23][C@:22]6([CH3:28])[C@H:17]5[C:15](=[O:16])[CH2:14][C@:13]4([CH3:29])[C@H:8]3[C@:7]2([OH:31])[CH3:30])[CH2:5]1

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 49864734HCID 49864734, compound2×

Product 1

HCID 11453970HCID 11453970, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

colorless crystals, mp: 240° C.; [α]D24−38.0° (c 2.41, CHCl3); 1H NMR (CDCl3) δ 5.31 (s, 1H), 5.00 (brs 1 H), 4.53 (q, J=7 Hz, 1H), 4.24 (brs 1H), 2.69 (dd, J=14.5, 3.5 Hz, 1H), 2.61 (d, J=6.5 Hz, 1H), 2.28 (m, 1H), 2.12 (m, 1H), 2.06 (m, 1H), 2.04 (s, 3H), 1.87 (m, 1H), 1.82 (m, 2H), 1.74 (m, 1H), 1.71 (m, 2H), 1.64 (m, 1H), 1.61 (dd, J=14.5, 4 Hz, 1H), 1.48 (m, 3H), 1.41 (s, 3H), 1.41 (m, 1H), 1.34 (m, 1H), 1.29 (s, 3H), 1.27 (m, 1H), 1.18 (m, 2H), 1.00 (s, 3H), 096 (s, 3H), 0.93 (d, J=7 Hz, 3H), 0.79 (m, 1H); 13C NMR (CDCl3) δ 170.6 s, 117.9 s, 101.3 d, 90.7 s, 84.7 s, 80.6 d, 70.0 d, 66.0 d, 64.3 d, 58.5 d, 56.1 s, 56.0 d, 41.1 d, 40.5 d, 39.2 t, 38.7 t, 35.9 s, 32.4 t, 33.7 t, 32.1 t, 32.1 t, 31.0 d, 29.0 q, 27.4 t, 25.6 t, 22.8 q, 21.4 q, 19.6 q, 14.4 q, 13.9 q; positive NOEs: H-6β/H-8, H-8/H-18, H-12β/H-21, H-12α/H-16, H-14/H-16, H-15β/H-18, H-16/H-17, H-17/H-21, and H-21/H-23α; IR (KBr) 3470, 3300, 1730, 1240 cm−1; EIMS m/z 500 (M−H2O), 485 (4), 442 (4), 372 (100%). The stereochemistry at C-18 was elucidated to be R configuration by positive NOEs between the proton pairs: H-18/H-8 and H-18/H-15β.

Workup

  1. custom39.2 t, 38.7 t, 35.9 s, 32.4 t, 33.7 t, 32.1 t, 32.1 t, 31.0 d, 29.0 q, 27.4 t, 25.6 t, 22.8 q, 21.4 q, 19.6 q, 14.4 q, 13.9 q

Sources & evidence

ORD record
ord-021e1168960a4313a71ccd01822f1810
Source dataset
uspto-grants-2011_08
Patent number
US08008346B2

Reaction notes

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