Hydrochloric Acid → ((3S,6S)-6-((2-((S)-2-amino-3,3-bis(4-fluorophenyl)propanamido)-6-fluorophenoxy)methyl)morpholin-3-yl)methyl (2,2,2-trifluoroethyl)carbamate

HRID 629748Notes

Reaction equation

HRID 629748 reaction equation
Cl.C(OC([NH:9][C@H:10]([C:26]([NH:28][C:29]1[CH:59]=[CH:58][CH:57]=[C:56]([F:60])[C:30]=1[O:31][CH2:32][C@H:33]1[O:38][CH2:37][C@@H:36]([CH2:39][O:40][C:41]([NH:43][CH2:44][C:45]([F:48])([F:47])[F:46])=[O:42])[N:35](C(OC(C)(C)C)=O)[CH2:34]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>[F:48][C:45]([F:46])([F:47])[CH2:44][NH:43][C:41](=[O:42])[O:40][CH2:39][C@@H:36]1[CH2:37][O:38][C@H:33]([CH2:32][O:31][C:30]2[C:56]([F:60])=[CH:57][CH:58]=[CH:59][C:29]=2[NH:28][C:26](=[O:27])[C@@H:10]([NH2:9])[CH:11]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH2:34][NH:35]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86726347tert-butyl (2S,5S)-2-[(2-{[N-(tert-butoxycarbonyl)-4-fluoro-beta-(4-fluorophenyl)-L-phenylalanyl]amino}-6-fluorophenoxy)methyl]-5-[({[(2,2,2-trifluoroethyl)amino]carbonyl}oxy)methyl]morpholine-4-carboxylate

Product 1

HCID 86577912((3S,6S)-6-((2-((S)-2-amino-3,3-bis(4-fluorophenyl)propanamido)-6-fluorophenoxy)methyl)morpholin-3-yl)methyl (2,2,2-trifluoroethyl)carbamateYield 96.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4M HCl (922 μl, 3.69 mmol) in dioxane was added to a solution of tert-butyl (2S,5S)-2-[(2-{[N-(tert-butoxycarbonyl)-4-fluoro-β-(4-fluorophenyl)-L-phenylalanyl]amino}-6-fluorophenoxy)methyl]-5-[({[(2,2,2-trifluoroethyl)amino]carbonyl}oxy)methyl]morpholine-4-carboxylate (310 mg, 0.369 mmol) in Dioxane (3.69 ml) at room temperature and the reaction stirred until complete by LC/MS (8 hrs). The solvent was removed in vacuo and ether was added to the residue. The desired product was filtered off to afford the title compound (253 mg, 0.355 mmol, 96% yield) as a white solid, MS (ESI): m/z=641.4 (M+H); 100% pure by LC/MS.

Workup

  1. customThe solvent was removed in vacuo and ether
  2. additionwas added to the residue
  3. filtrationThe desired product was filtered off

Sources & evidence

ORD record
ord-a265d4bbd64b43098d5ec5e46f68cad7
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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