Hydrochloric Acid → HCID 86726411, compound

HRID 629797Notes

Reaction equation

HRID 629797 reaction equation
Cl.[F:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([NH:34][C:35](=[O:60])[C@H:36]([CH:45]([C:53]2[CH:58]=[CH:57][C:56]([F:59])=[CH:55][CH:54]=2)[C:46]2[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=2)[NH:37][C:38]([O:40][CH2:41][CH:42]([CH3:44])[CH3:43])=[O:39])[C:8]=1[CH2:9][CH2:10][C@H:11]1[O:16][CH2:15][C@@H:14]([CH2:17][O:18][C:19](=[O:26])[NH:20][CH2:21][C:22]([F:25])([F:24])[F:23])[N:13](C(OC(C)(C)C)=O)[CH2:12]1>O1CCOCC1>[F:59][C:56]1[CH:57]=[CH:58][C:53]([CH:45]([C:46]2[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=2)[C@@H:36]([C:35]([NH:34][C:7]2[CH:6]=[N:5][CH:4]=[C:3]([F:2])[C:8]=2[CH2:9][CH2:10][C@H:11]2[O:16][CH2:15][C@@H:14]([CH2:17][O:18][C:19](=[O:26])[NH:20][CH2:21][C:22]([F:24])([F:23])[F:25])[NH:13][CH2:12]2)=[O:60])[NH:37][C:38]([O:40][CH2:41][CH:42]([CH3:43])[CH3:44])=[O:39])=[CH:54][CH:55]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86726412HCID 86726412, compound

Product 1

HCID 86726411HCID 86726411, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4M HCl in Dioxane (0.2 mL) was added directly to the product from step 2 (14 mg, 0.016 mmol) and the reaction stirred at RT for 1 hour. The solvent was removed in vacuo and the residue was dissolved in MeOH and loaded onto a 400 mg Porapak cartridge (preconditioned with 5 mL of MeOH). The cartridge was washed with 100 mL of MeOH, then the desired product was eluted with 10 mL of 2M NH3 in MeOH. The solvent was removed in vacuo to afford 4-fluoro-β-(4-fluorophenyl)-N-(5-fluoro-4-{2-[(2R,5S)-5-({[(2,2,2-trifluoroethyl)carbamoyl]oxy}methyl)morpholin-2-yl]ethyl}pyridin-3-yl)-Nα-[(2-methylpropoxy)carbonyl]-L-phenylalaninamide (10 mg, 0.014 mmol) as a tan solid, LC MS: RT=1.94 min, M+H=740.4 (4 min gradient).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in MeOH
  3. washThe cartridge was washed with 100 mL of MeOH
  4. washthe desired product was eluted with 10 mL of 2M NH3 in MeOH
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-25c831a2aa7e40f4a4e56fb5f392e236
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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