Triethylamine → HCID 492429, compound

HRID 1604008Notes

Reaction equation

[NH2:1][C@@H:2]1[C@@H:7]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[C@H:6]([C:15](=[O:23])[N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[O:5][C:4]([C:24]([O:26]C)=[O:25])=[CH:3]1.C(N(CC)CC)C>O>[NH2:1][C@@H:2]1[C@@H:7]([NH:8][C:9](=[O:14])[C:10]([F:12])([F:11])[F:13])[C@H:6]([C:15](=[O:23])[N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[O:5][C:4]([C:24]([OH:26])=[O:25])=[CH:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (4S,5R,6R)-4-amino-6-(dipropylcarbamoyl)-5-(2,2,2-trifluoroacetylamino)-5,6-dihydro-4H-pyran-2-carboxylic acid, methyl ester (0.34 g), triethylamine (1 ml) and water (2 ml) was heated at 50° C. for 2 hours. The solvent was removed in vacuo and the residue was co-evaporated with dioxane (×3) to afford the title compound as a white solid (330 mg). 1H NMR (250 MHz, D6 -DMSO) 9.40 (1H, s), 5.56 (1H, d, J=3 Hz), 4.70 (1H, d, J=9 Hz), 4.15 (1H, m), 3.85 (2H, m), 3.38 (2H, m), 3.15 (2H, m), 2.84 (2H, m), 1.47 (2H, m), 1.30 (2H, m), 0.72 (6H, m). Mass analysis: C15H22F3N3O5. 1.25 H2O. Required: C, 44.61; H, 6.11; N, 10.40. Found: C, 44.61; H, 6.10; N, 10.13.

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-ac54ab7d556f4a6582f2a15d8d0d051a
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990156

Reaction notes

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