Methanol → HCID 86690388, compound

HRID 513896Notes

Reaction equation

HRID 513896 reaction equation
C([O:4][C@H:5]([C@:16]12[CH2:51][C:50](=[O:52])[C:49]([CH:53]([CH3:55])[CH3:54])=[C:17]1[C@@H:18]1[C@@:31]([CH3:34])([CH2:32][CH2:33]2)[C@@:30]2([CH3:35])[C@@H:21]([C@:22]3([CH3:48])[C@@H:27]([CH2:28][CH2:29]2)[C:26]([CH3:37])([CH3:36])[C@@H:25]([O:38][C:39](=[O:47])[CH2:40][C:41]([CH3:46])([CH3:45])[C:42]([OH:44])=[O:43])[CH2:24][CH2:23]3)[CH2:20][CH2:19]1)[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)(=O)C.[C:56]([O-:59])([O-])=O.[Na+].[Na+].[CH3:62]O>>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][N:7]([CH2:6][C@@H:5]([C@:16]23[CH2:51][C:50](=[O:52])[C:49]([CH:53]([CH3:54])[CH3:55])=[C:17]2[C@@H:18]2[C@@:31]([CH3:34])([CH2:32][CH2:33]3)[C@@:30]3([CH3:35])[C@@H:21]([C@:22]4([CH3:48])[C@@H:27]([CH2:28][CH2:29]3)[C:26]([CH3:36])([CH3:37])[C@@H:25]([O:38][C:39](=[O:47])[CH2:40][C:41]([CH3:46])([CH3:45])[C:42]([OH:44])=[O:43])[CH2:24][CH2:23]4)[CH2:20][CH2:19]2)[OH:4])[C:56](=[O:59])[CH3:62])=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 10340Sodium CarbonateHCID 86690389HCID 86690389, compound

Product 1

HCID 86690388HCID 86690388, compoundYield 30%

Procedure

A mixture of 4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((R)-1-acetoxy-2-((4-chlorobenzyl)amino)ethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid (49) (150 mg, 0.192 mmol), Na2CO3 (20.37 mg, 0.192 mmol), in methanol (3 mL) was stirred for 3 h, then purified by preparative-HPLC to afford 4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((R)-2-(N-(4-chlorobenzyl)acetamido)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid (74) (45 mg, 30%) as a white solid. Compound exists as a mixture of rotomers; 1H NMR (500 MHz, METHANOL-d4) δ=7.43-7.27 (m, 2H), 7.28-7.11 (m, 2H), 5.30-4.09 (m, 6H), 3.55-2.09 (m, 11H), 2.09-0.78 (m, 44H); LC/MS: m/z calculated 779.5. found 780.4 (M+1)+.

Workup

  1. custompurified by preparative-HPLC

Sources & evidence

ORD record
ord-93a918f364ec4bf7832152eb260bd7b2
Source dataset
uspto-grants-2015_08
Patent number
US09102685B2

Reaction notes

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