Hydrochloric Acid → Phenylmethyl (2S)-4-({2'-fluoro-5'-[({[3-(4-piperidinylmethyl)phenyl]carbonyl}amino) methyl]-3-biphenylyl}methyl)-2-methyl-1-piperazinecarboxylate

HRID 2080323Notes

Reaction equation

HRID 2080323 reaction equation
CC(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:16]=[C:17]([C:21]([NH:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([F:55])=[C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][N:38]5[CH2:43][CH2:42][N:41]([C:44]([O:46][CH2:47][C:48]6[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=6)=[O:45])[C@@H:40]([CH3:54])[CH2:39]5)[CH:32]=4)[CH:30]=3)=[O:22])[CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=O)(C)C.Cl>O1CCOCC1>[F:55][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][NH:23][C:21]([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH:16]=2)=[O:22])=[CH:30][C:29]=1[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][N:38]2[CH2:43][CH2:42][N:41]([C:44]([O:46][CH2:47][C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)=[O:45])[C@@H:40]([CH3:54])[CH2:39]2)[CH:32]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57730435Phenylmethyl (2S)-4-[(5'-{[({3-[(1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-Piperidinyl)methyl]phenyl}carbonyl)amino]methyl}-2'-fluoro-3-biphenylyl)methyl]-2-methyl-1-piperazinecarboxylate

Product 1

HCID 11593255Phenylmethyl (2S)-4-({2'-fluoro-5'-[({[3-(4-piperidinylmethyl)phenyl]carbonyl}amino) methyl]-3-biphenylyl}methyl)-2-methyl-1-piperazinecarboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of phenylmethyl (2S)-4-[(5′-{[({3-[(1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-piperidinyl)methyl]phenyl}carbonyl)amino]methyl}-2′-fluoro-3-biphenylyl)methyl]-2-methyl-1-piperazinecarboxylate (673 mg, 0.90 mmol) in 5 mL of 1,4-dioxane was added 5 mL of 4M HCl in 1,4-dioxane. The mixture was stirred at room temperature for 30 min. After removal of the solvent, the crude was purified by Gilson reverse phase HPLC, eluting with acetonitrile/water/0.1% TFA (10/90 to 70/30, v/v, over 12 min), to give the title compound (390 mg, 67%). LC/MS: m/z, 649 (M+H), 1.69 min.

Workup

  1. customAfter removal of the solvent
  2. customthe crude was purified by Gilson reverse phase HPLC
  3. washeluting with acetonitrile/water/0.1% TFA (10/90 to 70/30, v/v, over 12 min)

Sources & evidence

ORD record
ord-d9043d816aa04eedb11a02d6fa945559
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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