Trifluoroacetic acid → HCID 54306624, compound

HRID 1415863Notes

Reaction equation

HRID 1415863 reaction equation
C(CCC(N)C(C(OCC)=O)(OC1CCOCC1)C(OCC)=O)(OC(C)(C)C)=O.FC(F)(F)C(O)=O.FC(F)(F)C([O-])=O.[CH2:44]([O:46][C:47]([C:49]([C:61]([O:63][CH2:64][CH3:65])=[O:62])([O:54][CH:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1)[CH2:50][CH2:51][CH2:52][NH3+:53])=[O:48])[CH3:45].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)C.CCOC(C)=O>[NH2:53][CH2:52][CH2:51][CH2:50][C:49]([C:47]([O:46][CH2:44][CH3:45])=[O:48])([O:54][CH:55]1[CH2:56][CH2:57][O:58][CH2:59][CH2:60]1)[C:61]([O:63][CH2:64][CH3:65])=[O:62]

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67552928HCID 67552928, compoundHCID 70347508HCID 70347508, compound

Product 1

HCID 54306624HCID 54306624, compoundYield 96.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 5-BOC-amino-2-ethoxycarbonyl-2-[4-tetrahydropyranyloxy]-pentanoate in CH2Cl2 (20 ml), cooled at 0-5° C., is added with trifluoroacetic acid (5 ml). After a night at room temperature, the mixture is evaporated under vacuum to obtain, after trituration of the residue in ethyl ether, 3.86 g of 4,4-diethoxycarbonyl-4-(4-tetrahydropyranyloxy)-butylammonium trifluoroacetate. A suspension of the salt in AcOEt (25 ml) is neutralized, under stirring at 0-5° C., by careful addition of a 5% sodium bicarbonate aqueous solution. After separating the organic phase and re-extracting the aqueous phase with AcOEt (3×5 ml), the combined organic phases are dried over Na2SO4, and solvent is evaporated off to obtain 2.73 g of ethyl 5-amino-2-ethoxycarbonyl-2-[4-tetrahydropyranyloxy]-pentanoate.

Workup

  1. waitAfter a night at room temperature
  2. customthe mixture is evaporated under vacuum
  3. customto obtain
  4. customAfter separating the organic phase
  5. extractionre-extracting the aqueous phase with AcOEt (3×5 ml)
  6. dry with materialthe combined organic phases are dried over Na2SO4, and solvent
  7. customis evaporated off

Sources & evidence

ORD record
ord-9659c91903884854b4ea815ceb0f43cd
Source dataset
uspto-grants-1999_06
Patent number
US05908863

Reaction notes

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