Potassium Bromide → HCID 15291529, compound

HRID 375013Notes

Reaction equation

HRID 375013 reaction equation
C1(N[C@H](C(O)=O)CC(C)C)C2C(=CC=CC=2)C=CC=1.[CH3:20][C:21]1[CH:22]=[C:23]2[C:32](=[CH:33][C:34]=1[CH3:35])[CH:31]=[CH:30][C:29]1[CH2:28][CH2:27][C@@H:26]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH:45]=[CH2:46])[C@@H:25]([NH:47][C:48](=[O:61])[C:49]3[CH:54]=[C:53]([N+:55]([O-:57])=[O:56])[CH:52]=[C:51]([N+:58]([O-:60])=[O:59])[CH:50]=3)[C:24]2=1.[K+].[Br-]>C(Cl)Cl>[CH3:20][C:21]1[CH:22]=[C:23]2[C:32](=[CH:33][C:34]=1[CH3:35])[CH:31]=[CH:30][C:29]1[CH2:28][CH2:27][CH:26]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH:45]=[CH2:46])[CH:25]([NH:47][C:48](=[O:61])[C:49]3[CH:50]=[C:51]([N+:58]([O-:60])=[O:59])[CH:52]=[C:53]([N+:55]([O-:57])=[O:56])[CH:54]=3)[C:24]2=1

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 14746886HCID 14746886, compoundHCID 86748436HCID 86748436, compound

Product 1

HCID 15291529HCID 15291529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By chromatographing the mixture of cis and trans isomers of CS-8 on a (S)-N-(1-naphthyl)leucine chiral stationary phase packed into a MPLC column, which chiral stationary phase is described by Pirkle, Deming and Burke in Chirality, 3:183-187 (1991) the contents of which are incorporated herein by reference, 2.68 g of enantiomerically pure cis CS-8, i.e., (cis)-6,7-Dimethyl-4-[N-(3,5-dinitrobenzoyl)]amino-3-(10-undecenyl)-1,2,3,4-tetrahydrophenanthrene, (last elUted enantiomer) was obtained, as were samples of the trans form of CS-8 (the first eluted enantiomer). Physical data for cis CS-8, obtained as a yellowish solid, were as follows: mp 181°-182° C., 1H NMR (CDCl3) δ 1.19-1.39 (m,14H), 1.42-1.77 (m,3H), 1.96-2.07 (m,4H), 2.36 (s,3H), 2.40 (s,3H), 3.03-3.10 (m,2H), 4.89-5.03 (m,2H), 5.74-5.88 (m,1H), 6.08 (dd, J=9.2 Hz, J= 2.8 Hz,1H), 6.20 (d, J=9.2 Hz,1H), 7.16 (d, J=8.2 Hz,1H), 7.52 (s,1H), 7.61 (d, J=8.2 Hz,1H), 7.85 (s,1H), 8.84 (d, J=1.7 Hz,2H), 9.08 (t, J=1.7 Hz,IH), IR (KBr) CM-1 3440, 2920, 2850, 1680, 1650, 1540, 1500, exact (EI) mass. calcd. for C34H41N3O5: 571.3046, Found: 571.3046, [α]D20 -126.2 (c 091, CH2Cl2).

Workup

  1. custom(last elUted enantiomer) was obtained
  2. customPhysical data for cis CS-8, obtained as a yellowish solid

Sources & evidence

ORD record
ord-08e69f47bf4d480393f2b577e8225f8e
Source dataset
uspto-grants-1996_01
Patent number
US05484530

Reaction notes

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