Hydrochloric Acid → 4-Fluoro-beta-(4-fluorophenyl)-N-(5-fluoro-4-{2-[(2R,5S)-5-({[(2,2,2-trifluoroethyl)carbamoyl]oxy}methyl)morpholin-2-yl]ethyl}pyridin-3-yl)-L-phenylalaninamide trihydrochloride

HRID 629739Notes

Reaction equation

HRID 629739 reaction equation
[ClH:1].C(OC([NH:9][C@H:10]([C:26]([NH:28][C:29]1[CH:30]=[N:31][CH:32]=[C:33]([F:60])[C:34]=1[CH2:35][CH2:36][C@H:37]1[O:42][CH2:41][C@@H:40]([CH2:43][O:44][C:45](=[O:52])[NH:46][CH2:47][C:48]([F:51])([F:50])[F:49])[N:39](C(OC(C)(C)C)=O)[CH2:38]1)=[O:27])[CH:11]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=O)(C)(C)C>O1CCOCC1>[ClH:1].[ClH:1].[ClH:1].[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH:11]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[C@@H:10]([C:26]([NH:28][C:29]2[CH:30]=[N:31][CH:32]=[C:33]([F:60])[C:34]=2[CH2:35][CH2:36][C@H:37]2[O:42][CH2:41][C@@H:40]([CH2:43][O:44][C:45](=[O:52])[NH:46][CH2:47][C:48]([F:50])([F:49])[F:51])[NH:39][CH2:38]2)=[O:27])[NH2:9])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86726338tert-Butyl (2R,5S)-2-[2-(3-{[N-(tert-butoxycarbonyl)-4-fluoro-beta-(4-fluorophenyl)-L-phenylalanyl]amino}-5-fluoropyridin-4-yl)ethyl]-5-({[(2,2,2-trifluoroethyl)carbamoyl]oxy}methyl)morpholine-4-carboxylate

Product 1

HCID 867263394-Fluoro-beta-(4-fluorophenyl)-N-(5-fluoro-4-{2-[(2R,5S)-5-({[(2,2,2-trifluoroethyl)carbamoyl]oxy}methyl)morpholin-2-yl]ethyl}pyridin-3-yl)-L-phenylalaninamide trihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4M HCl (3.54 mL, 14.17 mmol) in dioxane was added to a solution of tert-Butyl (2R,5S)-2-[2-(3-{[N-(tert-butoxycarbonyl)-4-fluoro-β-(4-fluorophenyl)-L-phenylalanyl]amino}-5-fluoropyridin-4-yl)ethyl]-5-({[(2,2,2-trifluoroethyl)carbamoyl]oxy}methyl)morpholine-4-carboxylate (1.19 g, 1.42 mmol) in Dioxane (14 mL) at ambient temperature and the reaction stirred for 4 hours. The solvent was removed in vacuo and ether was added to the residue. The title compound was filtered off as a white solid (1.00 g, 1.34 mmol, 94% yield), MS (ESI): m/z=640.40 (MH+); 100% pure by LCMS.

Workup

  1. customThe solvent was removed in vacuo and ether
  2. additionwas added to the residue

Sources & evidence

ORD record
ord-ac0125654b0d4128a880aa24caadcca4
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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