Trifluoroacetic acid → HCID 19969480, compound

HRID 2400055Notes

Reaction equation

HRID 2400055 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[C:34]([N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[N:33]=[C:32]([N:41]3[CH2:45][CH2:44][CH2:43][CH2:42]3)[N:31]=2)[CH2:26][CH2:25]1)=[O:23])=O)(C)(C)C.[OH-].[Na+]>C(Cl)Cl>[NH:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][O:21][C:22]([N:24]1[CH2:25][CH2:26][N:27]([C:30]2[CH:35]=[C:34]([N:36]3[CH2:37][CH2:38][CH2:39][CH2:40]3)[N:33]=[C:32]([N:41]3[CH2:45][CH2:44][CH2:43][CH2:42]3)[N:31]=2)[CH2:28][CH2:29]1)=[O:23]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 53633805HCID 53633805, compound

Product 1

HCID 19969480HCID 19969480, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.174 ml of trifluoroacetic acid are dropped into a solution of 100 mg of (-)-N'-[(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)methoxycarbonyl]-N-[2,6-bis(pyrrolidin-1-yl)pyrimidin-4-yl)piperazine in 4 ml of methylene chloride. After about 18 hours, the reaction mixture is added with a 1N sodium hydroxide aqueous solution and it is extracted with methylene chloride (3×3 ml). The combined organic extracts are washed with water (2×2 ml), dried over sodium sulfate and solvent is evaporated off under reduced pressure. The residue is crystallized from 9:1 diisopropyl ether/ethyl acetate, to give 65 mg of (+)-N'-[(pyrrolidin-2-yl)methoxycarbonyl]-N-[2,6-bis(pyrrolidin-1-yl)pyrimidin-4-yl]piperazine, m.p. 137°-138° C., [α]D =8.7° (c=0.23 in EtOH).

Workup

  1. extractionis extracted with methylene chloride (3×3 ml)
  2. washThe combined organic extracts are washed with water (2×2 ml)
  3. dry with materialdried over sodium sulfate and solvent
  4. customis evaporated off under reduced pressure
  5. customThe residue is crystallized from 9:1 diisopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-59c3a0d8e5c044d08985147ebc05f4d1
Source dataset
uspto-grants-1995_09
Patent number
US05453423

Reaction notes

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