Trifluoroacetic acid → HCID 54127247, compound

HRID 366217Notes

Reaction equation

HRID 366217 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:45])([CH3:44])[CH2:9][O:10][CH2:11][C:12](=[O:43])[N:13]([CH3:42])[C@@H:14]([C:26](=[O:41])[N:27]([CH3:40])[C@@H:28]([C:36](=[O:39])[NH:37][CH3:38])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[NH2:7][C:8]([CH3:45])([CH3:44])[CH2:9][O:10][CH2:11][C:12]([N:13]([C@H:14]([CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[C:26]([N:27]([CH3:40])[C@@H:28]([C:36](=[O:39])[NH:37][CH3:38])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:41])[CH3:42])=[O:43]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium Bicarbonate2×HCID 53978277HCID 53978277, compound

Product 1

HCID 54127247HCID 54127247, compoundYield 114.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(1,1-Dimethyl-2-((N-methyl-N-((1R)-1-(N-methyl-N-((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(1-naphthyl)-ethyl)carbamoyl)methoxy)ethyl)carbamic acid tert-butylester (0.26 g; 0.41 mmol) was dissolved in methylene chloride (3 mL) and trifluoroacetic acid (2 mL) was added. The reaction mixture was stirred for 5 min at room temperature. Methylene chloride (5 mL), an aqueous solution of sodium hydrogen carbonate (saturated) and sodium hydrogen carbonate (solid) were added until pH 8. The aqueous phase was extrated with methylene chloride (3×15 mL) and the combined organic layers were dried (magnesium sulfate). The solvent was removed in vacuo to afford 0.25 g of the title compound.

Workup

  1. dry with materialthe combined organic layers were dried (magnesium sulfate)
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a74d112b3f154f9094d2b03901523711
Source dataset
uspto-grants-2000_10
Patent number
US06127391

Reaction notes

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