Trifluoroacetic acid → HCID 54194123, compound

HRID 2287899Notes

Reaction equation

HRID 2287899 reaction equation
C(O[C:6]([N:8](C)[NH:9][C:10](=[O:54])[C@H:11]([N:19]([C:21](=[O:53])[C@H:22]([N:34]([C:36]([O:38][CH2:39][CH:40]1[C:52]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[C:46]2[C:41]1=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:37])[CH3:35])[CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1)[CH3:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:42]1[C:41]2[CH:40]([CH2:39][O:38][C:36](=[O:37])[N:34]([CH3:35])[C@@H:22]([C:21](=[O:53])[N:19]([CH3:20])[C@@H:11]([C:10]([NH:9][NH:8][CH3:6])=[O:54])[CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=3)[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]=2[CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium Bicarbonate2×HCID 53993942HCID 53993942, compound

Product 1

HCID 54194123HCID 54194123, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N'-[(2R)-2-(N-((2R)-2-[N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-methylamino]-3-(2-naphthyl)propionyl)-N-methylamino)-3-phenylpropionyl]-N-methylhydrazinecarboxylic acid tert-butyl ester (0.27 g, 0.36 mmol) in methylene chloride (2 ml) at 0° C. was added trifluoroacetic acid (2 ml) and the mixture was stirred for 90 min. Then methylene chloride (50 ml) and saturated sodium bicarbonate (5 ml) was added and the mixture was titrated with solid sodium bicarbonate until pH=7. The water layer was separated and extracted with methylene chloride (20 ml) and the combined organic layers were washed with brine (10 ml), dried (MgSO4), filtered and concentrated in vacuo to give 0.18 g (78%) of N-methyl-N-((1R)-1-(N-methyl-N-[(1R)-1-(N'-methylhydrazinocarbonyl)-2-phenylethyl]carbamoyl)-2-(2-naphthyl)ethyl)carbamic acid ((9H-fluoren-9-yl)methyl) ester as white amorphous powder.

Workup

  1. customThe water layer was separated
  2. extractionextracted with methylene chloride (20 ml)
  3. washthe combined organic layers were washed with brine (10 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51f762cce13447a188b681b913ab675c
Source dataset
uspto-grants-2000_07
Patent number
US06083908

Reaction notes

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