Lithium Bromide → HCID 67777449, compound

HRID 406860Notes

Reaction equation

HRID 406860 reaction equation
C[O:2][C:3]([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])[CH: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:28]=[C:29]([CH:33]=[CH:34][CH:35]=2)[C:30]([OH:32])=[O:31])=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)=[O:4].[Br-].[Li+]>CN(C=O)C>[C:30]([C:29]1[CH:28]=[C:27]([C:14]2[C:15]([CH3:26])([CH3:25])[C@H:16]3[C@:11]([CH3:36])([CH2:12][CH:13]=2)[CH:10]2[C@:19]([CH3:24])([C@@:20]4([CH3:23])[C@H:7]([CH2:8][CH2:9]2)[C@H:6]2[C@H:37]([C:40]([CH3:42])=[CH2:41])[CH2:38][CH2:39][C@:5]2([C:3]([OH:4])=[O:2])[CH2:22][CH2:21]4)[CH2:18][CH2:17]3)[CH:35]=[CH:34][CH:33]=1)([OH:32])=[O:31]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 67777450HCID 67777450, compound

Product 1

HCID 67777449HCID 67777449, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-((1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-3a-(methoxycarbonyl)-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 (140 mg, 0.244 mmol) and lithium bromide (425 mg, 4.89 mmol) in DMF (2 mL) was heated to 100° C. for 2 days. TLC indicated starting material was consumed and desired product was observed. The reaction mixture was filtered and the clear solution was purified by HPLC to provide the desired product (1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-9-(3-carboxyphenyl)-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]chrysene-3a-carboxylic acid as a white solid (25 mg, 17%). LCMS: m/e 557.48 (M−H)−, 5.67 min (method 6). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.89 (s, 3H), 0.91 (s, 3H), 0.96 (s, 3H), 0.98 (s, 3H), 1.00 (s, 3H), 1.01-1.76 (m, 17H), 1.68 (s, 3H), 1.79-1.89 (m, 2H), 2.04-2.19 (m, 2H), 2.27-2.32 (m, 1H), 2.93-3.05 (m, 1H), 4.59 (s, 1H), 4.73 (d, J=2.01 Hz, 1H), 5.26 (d, J=4.77 Hz, 1H), 7.29-7.35 (m, 1H), 7.40 (t, J=7.65 Hz, 1H), 7.66 (s, 1H), 7.83 (d, J=7.53 Hz, 1H).

Workup

  1. customwas consumed
  2. filtrationThe reaction mixture was filtered
  3. customthe clear solution was purified by HPLC

Sources & evidence

ORD record
ord-69fcf85f505d45d09efeb9ecac5043ed
Source dataset
uspto-grants-2014_06
Patent number
US08754068B2

Reaction notes

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