Trifluoroacetic acid → HCID 69012430, compound

HRID 1879810Notes

Reaction equation

HRID 1879810 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-ee64bceb74c547b8902bd2b1693f4bba
Source dataset
uspto-grants-2012_11
Patent number
US08318705B2

Reaction notes

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