Trifluoroacetic acid → HCID 69012430, compound

HRID 1630452Notes

Reaction equation

HRID 1630452 reaction equation
[C:1]([O:4][CH2:5][CH:6]([N:12]([CH3:21])[CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>ClCCl>[C:1]([O:4][CH2:5][CH:6]([N:12]([CH3:21])[CH2:13][C:14]([OH:16])=[O:15])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86635761HCID 86635761, compound

Product 1

HCID 69012430HCID 69012430, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 2-{[1,3-bis(acetyloxy)propan-2-yl](methyl)amino}acetate (1.32 g, 4.3 mmol) was stirred in a solution of 20% TFA:dichloromethane (20 ml) for 5 hours. Upon completion of reaction (assessed by LC-MS) the reaction was concentrated in vacuo and re-dissolved in dichloromethane (10 ml). The HCl salt was treated with polymer supported-diisopropylamine (3.5 g) for 18 hours and the resin removed by filtration. The resin was washed with MeCN (3×10 ml) and the title compound isolated by concentration in vacuo. (1.0 g, 93%) 1H NMR (500 MHz, CHLOROFORM-d) δ 4.18 (4H, d, 6.4 Hz), 3.41 (2H, s), 3.17-3.29 (1H, m), 2.50 (3H, s), 2.11 (6H, s).

Workup

  1. customUpon completion of reaction (assessed by LC-MS) the reaction
  2. concentrationwas concentrated in vacuo
  3. dissolutionre-dissolved in dichloromethane (10 ml)
  4. additionThe HCl salt was treated with polymer
  5. customfor 18 hours
  6. customthe resin removed by filtration
  7. washThe resin was washed with MeCN (3×10 ml)

Sources & evidence

ORD record
ord-317d0e76223f4fc59a2421e07a45bb37
Source dataset
uspto-grants-2014_07
Patent number
US08791134B2

Reaction notes

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