HCID 86754848, compound → HCID 57128419, compound

HRID 1604005Notes

Reaction equation

[C:1]([NH:4][C@H:5]1[C@H:10]([C:11](=[O:30])[N:12]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH3:15])[O:9][C:8]([C:31]([O:33]C)=[O:32])=[CH:7][C@@H:6]1[OH:35])(=[O:3])[CH3:2]>C(N(CC)CC)C>[C:1]([NH:4][C@H:5]1[C@H:10]([C:11](=[O:30])[N:12]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH3:15])[O:9][C:8]([C:31]([OH:33])=[O:32])=[CH:7][C@@H:6]1[OH:35])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (4S,5R,6R)-5-acetylamino-4-hydroxy-6-[(2-biphenyl-4-yl-ethyl)propylcarbamoyl]-5,6-dihydro-4H-pyran-2-carboxylic acid, methyl ester (0.89 g) water (5 ml) and triethylamine (5 ml) was heated at 50° C. for 6 hours. The solvent was then removed in vacuo and the residue was co-evaporated with dioxane (×3) to afford the title compound as an off white solid (0.87 g). 1H NMR (250 MHz, D6 -DMSO rotamers) 7.96 (1H, d, J=8 Hz), 7.60 (4H, m), 7.45 (2H, m), 7.33 (3H, m), 5.72 (1H, m), 5.15 (1H, m), 4.90 (1H, m), 4.25 (1H, m), 3.87 (1H, m), 3.60-2.95 (8H, m), 1.80+1.75 (3H, 2×s), 1.55 (1H, m), 1.46 (1H, m), 0.83 (3H, m). Mass analysis: C26H30N2O6. 1.0 H2O. 0.6 C6H15N Required: C, 65.20; H, 7.58; N, 6.68. Found: C, 65.40; H, 7.59; N, 6.44.

Workup

customThe solvent was then removed in vacuo

Sources & evidence

ORD record: ord-ce435490f7214418a4a6fd8b3e936ce8
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990156

Reaction notes

Loading…