Trifluoroacetic acid → HCID 22344765, compound

HRID 583949Notes

Reaction equation

HRID 583949 reaction equation
C([O:5][C:6]([CH2:8][N:9]1[C:16](=[O:17])[CH2:15][CH2:14][N:13]([CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])[C:12](=[O:26])[CH2:11][CH2:10]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:19]([CH2:18][N:13]1[C:12](=[O:26])[CH2:11][CH2:10][N:9]([CH2:8][C:6]([OH:7])=[O:5])[C:16](=[O:17])[CH2:15][CH2:14]1)([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20820309HCID 20820309, compound2×

Product 1

HCID 22344765HCID 22344765, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.4 g of tert-butyl (5-tert-butoxycarbonylmethyl-2,6-dioxoperhydro-1,5-diazocin-1-yl)acetate (starting material A3) are dissolved in 6 ml of dichloromethane, and 6 ml of trifluoroacetic acid are added. The mixture is stirred overnight and then concentrated using a rotary evaporator, and the residue is triturated with ethyl acetate/petroleum ether (1:1). The residue is filtered off with suction and dried under reduced pressure. This gives 0.89 g of the title compound which starts to melt at 250° C. (decomposition); the mass spectrum shows the molecular peaks MH+ and MNH4+ at 259 and 276 Da, respectively.

Workup

  1. concentrationconcentrated
  2. customa rotary evaporator
  3. customthe residue is triturated with ethyl acetate/petroleum ether (1:1)
  4. filtrationThe residue is filtered off with suction
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-a03940d163f64244a45841500449bad9
Source dataset
uspto-grants-2005_08
Patent number
US06924305B2

Reaction notes

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