Trifluoroacetic acid → HCID 87404217, compound

HRID 588919Notes

Reaction equation

HRID 588919 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]([CH3:23])([CH3:22])[NH:5][C:6](=[O:21])[C@H:7]([CH2:16][O:17][C:18]#[C:19][CH3:20])[NH:8]C(OC(C)(C)C)=O.[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26]>C(Cl)Cl>[F:28][C:27]([F:30])([F:29])[C:25]([OH:31])=[O:26].[CH3:1][O:2][C:3](=[O:24])[C:4]([CH3:23])([CH3:22])[NH:5][C:6](=[O:21])[C@H:7]([CH2:16][O:17][C:18]#[C:19][CH3:20])[NH2:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 87403827HCID 87403827, compound

Product 1

HCID 87404217HCID 87404217, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Purified N-tert-butoxycarbonyl O-propynyl-L-seryl α,α-dimethylglycine methyl ester 14 (2.27 g, 6.63 mmol) was dissolved in 50% (v/v) TFA in CH2Cl2 and the reaction mixture stirred for 1 h 10 min at room temperature. The solvent and bulk of excess TFA were evaporated and CH2Cl2 (3×20 mL) added and evaporated. Diethyl ether (25 mL) was added causing a white solid to precipitate on standing. The Et2O was decanted off and the residue washed with more Et2O (2×25 mL). After decantation of the Et2O the residue was dried under high vacuum affording the title compound as a white solid (2.10 g, 89%); 1H NMR (200 MHz, DMSO-d6) δ 8.95 (s, 1H, NH), 8.31 (br s, 3H, NH3+), 4.20 (d, J=2.4 Hz, 2H, CH2CCH), 4.02 (dd, J=5.8, 3.8 Hz, 1H, CαH or CHH), 3.88-3.67 (m, 2H, CH2 or CαH/CHH), 3.57 (s, 3H, OCH3), 3.52 (t, J=2.3 Hz, 1H, CCH), 1.39 (s, 3H, CH3), 1.36 (s, 3H, CH3); 13C NMR (75 MHz, DMSO-d6) δ 173.9, 165.7, 158.3 (q, JCF=31 Hz), 117.2 (q, JCF=298 Hz), 79.5, 78.0, 68.0, 58.1, 55.5, 52.1, 52.0, 24.7; HRMS (m/z): M+ calcd. for C11H19N2O4, 243.1344. found, 243.1335; Anal. Calcd. for C13H19F3N2O6: C, 43.82; H, 5.38; N, 7.86. Found: C, 43.8; H, 5.4; N, 7.8.

Workup

  1. customThe solvent and bulk of excess TFA were evaporated
  2. additionCH2Cl2 (3×20 mL) added
  3. customevaporated
  4. additionDiethyl ether (25 mL) was added
  5. customto precipitate on standing
  6. customThe Et2O was decanted off
  7. washthe residue washed with more Et2O (2×25 mL)
  8. dry with materialAfter decantation of the Et2O the residue was dried under high vacuum

Sources & evidence

ORD record
ord-c0664855616b4caf9cda52b093f9a55c
Source dataset
uspto-grants-2016_01
Patent number
US09227995B2

Reaction notes

Loading…