Phosphoric Acid → HCID 86692347, compound

HRID 1400991Notes

Reaction equation

HRID 1400991 reaction equation
[NH2:1][C@:2]12[CH2:43][CH2:42][C@@H:41]([C:44]([CH3:46])=[CH2:45])[C@@H:3]1[C@@H:4]1[C@@:17]([CH3:20])([CH2:18][CH2:19]2)[C@@:16]2([CH3:21])[C@@H:7]([C@:8]3([CH3:40])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:23])([CH3:22])[C:11]([C:24]2[CH2:29][CH2:28][C@@H:27]([C:30]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])[CH2:26][CH:25]=2)=[CH:10][CH2:9]3)[CH2:6][CH2:5]1.Br[CH2:48][CH2:49]Cl.P(=O)(O)(O)O.[K]>C(#N)C>[N:1]1([C@:2]23[CH2:43][CH2:42][C@@H:41]([C:44]([CH3:46])=[CH2:45])[C@@H:3]2[C@@H:4]2[C@@:17]([CH3:20])([CH2:18][CH2:19]3)[C@@:16]3([CH3:21])[C@@H:7]([C@:8]4([CH3:40])[C@@H:13]([CH2:14][CH2:15]3)[C:12]([CH3:23])([CH3:22])[C:11]([C:24]3[CH2:29][CH2:28][C@@H:27]([C:30]([O:32][CH2:33][C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)=[O:31])[CH2:26][CH:25]=3)=[CH:10][CH2:9]4)[CH2:6][CH2:5]2)[CH2:49][CH2:48]1

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 78491-Bromo-2-ChloroethaneHCID 5462222PotassiumHCID 86692345(R)-benzyl 4-((1R,3 aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3 a-amino-5 a,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)cyclohex-3-enecarboxylate

Product 1

HCID 86692347HCID 86692347, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a sealable vial was added (R)-benzyl 4-((1R,3 aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-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)cyclohex-3-enecarboxylate (0.075 g, 0.120 mmol), 1-bromo-2-chloroethane (0.100 mL, 1.202 mmol), and phosphoric acid, potassium salt (0.128 g, 0.601 mmol). The mixture was diluted with acetonitrile (1.5 mL), flushed with nitrogen, then the vial was sealed and heated to 120° C. After 24 h of heating, the mixture was cooled to rt and was filtered to remove solids. The solids were washed with dichloromethane and the filtrate was concentrated under reduced pressure to give (R)-benzyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(aziridin-1-yl)-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)cyclohex-3-enecarboxylate as an off-white solid that was used in the next step with no additional purification. LCMS: m/e 650.7 (M+H)+, 2.22 min (method 1).

Workup

  1. customflushed with nitrogen
  2. customthe vial was sealed
  3. temperatureAfter 24 h of heating
  4. temperaturethe mixture was cooled to rt
  5. filtrationwas filtered
  6. customto remove solids
  7. washThe solids were washed with dichloromethane
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4c01860ba48f4007abdf2ef28404c363
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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