Hydrochloric Acid → HCID 86690386, compound

HRID 513895Notes

Reaction equation

HRID 513895 reaction equation
C([O:4][C@@H:5]([C@:19]12[CH2:54][C:53](=[O:55])[C:52]([CH:56]([CH3:58])[CH3:57])=[C:20]1[C@@H:21]1[C@@:34]([CH3:37])([CH2:35][CH2:36]2)[C@@:33]2([CH3:38])[C@@H:24]([C@:25]3([CH3:51])[C@@H:30]([CH2:31][CH2:32]2)[C:29]([CH3:40])([CH3:39])[C@@H:28]([O:41][C:42](=[O:50])[CH2:43][C:44]([CH3:49])([CH3:48])[C:45]([OH:47])=[O:46])[CH2:27][CH2:26]3)[CH2:23][CH2:22]1)[CH2:6][N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:8](=[O:10])[CH3:9])(=O)C.[OH-].[K+].Cl>C(O)C.C1(C)C=CC=CC=1>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:7]([CH2:6][C@H:5]([C@:19]23[CH2:54][C:53](=[O:55])[C:52]([CH:56]([CH3:57])[CH3:58])=[C:20]2[C@@H:21]2[C@@:34]([CH3:37])([CH2:35][CH2:36]3)[C@@:33]3([CH3:38])[C@@H:24]([C@:25]4([CH3:51])[C@@H:30]([CH2:31][CH2:32]3)[C:29]([CH3:39])([CH3:40])[C@@H:28]([O:41][C:42](=[O:50])[CH2:43][C:44]([CH3:48])([CH3:49])[C:45]([OH:47])=[O:46])[CH2:27][CH2:26]4)[CH2:23][CH2:22]2)[OH:4])[C:8](=[O:10])[CH3:9])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86690387HCID 86690387, compound

Product 1

HCID 86690386HCID 86690386, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((S)-1-acetoxy-2-(N-(4-chlorobenzyl)acetamido)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 (72) (150 mg, 0.182 mmol) in ethanol (2 mL) and toluene (2 mL) was added potassium hydroxide (40.9 mg, 0.729 mmol). The reaction mixture was stirred at rt for min. The reaction mixture was neutralized with aqueous 1 N HCl to pH=7 and concentrated to obtain a residue. The residue was extracted with DCM, washed with water and dried to yield the crude product which was purified by preparative-HPLC to afford 4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((S)-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 (73) (40 mg, 28%) as a white solid. Compound exists as a mixture of rotomers; 1H NMR (400 MHz, DMSO-d6) δ=12.18 (br. s., 1H), 7.52-7.14 (m, 4H), 5.03-3.77 (m, 5H), 3.39-2.80 (m, 3H), 2.62-2.54 (m, 1H), 2.27 (t, J=17.2 Hz, 1H), 2.20-0.58 (m, 51H);

Workup

  1. concentrationconcentrated
  2. customto obtain a residue
  3. extractionThe residue was extracted with DCM
  4. washwashed with water
  5. customdried
  6. customto yield the crude product which
  7. customwas purified by preparative-HPLC

Sources & evidence

ORD record
ord-b8f4d6935ec54abcaaf3425dc14a5b56
Source dataset
uspto-grants-2015_08
Patent number
US09102685B2

Reaction notes

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