1,2-Dichloroethane → HCID 67774931, compound

HRID 2405512Notes

Reaction equation

HRID 2405512 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:52])[CH2:5][CH2:6][NH:7][C:8]([C@:10]12[CH2:48][CH2:47][C@@H:46]([C:49]([CH3:51])=[CH2:50])[C@@H:11]1[C@@H:12]1[C@@:25]([CH3:28])([CH2:26][CH2:27]2)[C@@:24]2([CH3:29])[C@@H:15]([C@:16]3([CH3:45])[C@@H:21]([CH2:22][CH2:23]2)[C:20]([CH3:31])([CH3:30])[C:19]([C:32]2[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:34][CH:33]=2)=[CH:18][CH2:17]3)[CH2:14][CH2:13]1)=[O:9].[C:53]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])(=[O:60])[CH2:54][CH2:55][C:56](OC)=[O:57].C(Cl)CCl>ClCCl>[C:56]([O:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][NH:7][C:8]([C@:10]12[CH2:48][CH2:47][C@@H:46]([C:49]([CH3:51])=[CH2:50])[C@@H:11]1[C@@H:12]1[C@@:25]([CH3:28])([CH2:26][CH2:27]2)[C@@:24]2([CH3:29])[C@@H:15]([C@:16]3([CH3:45])[C@@H:21]([CH2:22][CH2:23]2)[C:20]([CH3:31])([CH3:30])[C:19]([C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])=[CH:43][CH:44]=2)=[CH:18][CH2:17]3)[CH2:14][CH2:13]1)=[O:9])[CH3:52])(=[O:57])[CH2:55][CH2:54][C:53]([O:61][C:62]([CH3:64])([CH3:63])[CH3:65])=[O:60]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 139819Butanedioc acid tert-butyl methyl esterHCID 67775029HCID 67775029, compound

Product 1

HCID 67774931HCID 67774931, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-((2-hydroxyethyl)(methyl)amino)ethylcarbamoyl)-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)benzoate (40 mg, 0.056 mmol), tert-butyl methyl succinate (21.06 mg, 0.112 mmol), Hunig'sBase (0.049 mL, 0.280 mmol) and EDC (21.45 mg, 0.112 mmol) in dichloromethane (1 mL) was stirred at 20° C. for 12 hours. LCMS indicated the formation of desired product. The reaction mixture was quenched with distilled water, extracted with DCM (3×4 mL). All the extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the crude including the title compound as a white solid (40 mg, 82%). LCMS: m/e 871.43 (M+H)+, 3.93 min (method 1).

Sources & evidence

ORD record
ord-a982ff0bd6744878bc600751c029bcf3
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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