Triethylamine → HCID 11790368, compound

HRID 1601742Notes

Reaction equation

HRID 1601742 reaction equation
S(=O)(=O)(O)O.[NH2:6][CH:7]([CH:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]#[N:9].C(N(CC)CC)C.[CH3:25][OH:26].[OH2:27]>>[C:8]([CH:7]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:17][C:25](=[O:26])[NH:6]1)(=[O:27])[NH2:9]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 21832279HCID 21832279, compoundHCID 22242641Methanol--water (1/1)

Product 1

HCID 11790368HCID 11790368, compound

Procedure

To a solution of α-amino-β-hydroxy-β-phenylpropane nitrile bisulphate salt (6 g, 23 mmoles) in 50 ml MeOH/H2O (m:m/1:1) triethylamine (TEAM) (9.6 g, 69.2 mmoles) was added. Subsequently, for 6 hours CO2 was bubbled through the solution at 40° C. During the reaction the pH of the solution fell from 9.7 to 7.8. A white solid substance crystallized out of the solution. This substance was filtered off and dried in a vacuum. The yield was 4.7 g (22.8 moles, 99 wt. % ), obtained in the form of white crystals having a melting point: 249-250° C.; 1H NMR (200 MHz, DMSO) d (ppm): 3.30 (0.5H, s, H2O), 4.42 (1H, δ, J=8.37 Hz, NCHCO), 5.79 (1H, d, J=8.37 Hz, OCHPh), 6.85 (1H, s, NH), 7.20 (1H, s, NH), 7.30 (5H, m, Ph), 8.00 (1H, s, NH); 13C NMR (200 MHz, DMSO) δ (ppm): 59.41 (NCHCO), 78.75 (OCHHPh), 126.82 (Ph), 127.94 (Ph), 128.41 (Ph), 135.44 (Ph), 15.02 (NC=OO), 169.77 (C=ONH2); IR (KBr,cm-1): 3396 (NH2), 3273 (NH2), 3200, 1740 (C=O), 1719, 1684 (C=O), 1611 Mass (El): 206 M, 189, 163, 105, 77, 44. The experiment was repeated under different conditions. The results are shown in Table 1.

Workup

  1. customSubsequently, for 6 hours CO2 was bubbled through the solution at 40° C
  2. customDuring the reaction the pH of the solution
  3. customA white solid substance crystallized out of the solution
  4. filtrationThis substance was filtered off
  5. customdried in a vacuum
  6. customThe yield was 4.7 g (22.8 moles, 99 wt. % ), obtained in the form of white crystals

Sources & evidence

ORD record
ord-80a8df74653c4d5297bae34d4b0316db
Source dataset
uspto-grants-1999_11
Patent number
US05977406

Reaction notes

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