Trifluoroacetic acid → HCID 131734453, compound

HRID 588923Notes

Reaction equation

HRID 588923 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][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.[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26]>C(Cl)Cl>[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26].[CH3:1][O:2][C:3](=[O:22])[CH2:4][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 123324359HCID 123324359, compound

Product 1

HCID 131734453HCID 131734453, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-tert-butoxycarbonyl O-propynyl L-seryl glycine methyl ester (2.52 g, 8.02 mmol) was dissolved in CH2Cl2 (15 mL). Trifluoroacetic acid (15 mL) was added and the reaction mixture stirred for 2 h at room temperature. The solvent and bulk of excess TFA were removed and the residue washed with Et2O (2×15 mL). The diethyl ether was decanted off and the residue dried under vacuum before being redissolved in CH2Cl2 (70 mL). The solvent was evaporated and the residue dried under high vacuum overnight affording a brown, viscous oil (2.32 g, 88%); δH (200 MHz; d6-DMSO) 8.97 (1H, t, J 6, NH), 8.31 (3H, br s, NH3+), 4.21 (2H, d, J 2, CH2CCH), 4.16-4.05 (1H, m, CαH(propSer)), 3.96 (2H, d, J 6, CαH2(Gly)), 3.83 (1H, dd, J 11 and 4, CHH), 3.74 (1H, dd, J 11 and 6, CHH), 3.65 (3H, s, OCH3), 3.55 (1H, t, J 2, CCH).

Workup

  1. customThe solvent and bulk of excess TFA were removed
  2. washthe residue washed with Et2O (2×15 mL)
  3. customThe diethyl ether was decanted off
  4. customthe residue dried under vacuum
  5. dissolutionbefore being redissolved in CH2Cl2 (70 mL)
  6. customThe solvent was evaporated
  7. customthe residue dried under high vacuum overnight

Sources & evidence

ORD record
ord-db4e590487f04c559afed295c8d6982c
Source dataset
uspto-grants-2016_01
Patent number
US09227995B2

Reaction notes

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