L-Valinol → (S)-2-((2R,3R)-2-(3-Chlorophenyl)-3-(4-chlorophenyl)-3-hydroxypropyl)-N-((S)-1-hydroxy-3-methylbutan-2-yl)-2-methylpent-4-enamide

HRID 1048525Notes

Reaction equation

[NH2:1][C@@H:2]([CH:5]([CH3:7])[CH3:6])[CH2:3][OH:4].[CH2:8]([C@@:11]1([CH3:32])[CH2:16][C@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C@H:14]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[O:13][C:12]1=[O:31])[CH:9]=[CH2:10]>C(OCC)(=O)C>[Cl:23][C:19]1[CH:18]=[C:17]([C@H:15]([C@H:14]([C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[OH:13])[CH2:16][C@:11]([CH3:32])([CH2:8][CH:9]=[CH2:10])[C:12]([NH:1][C@@H:2]([CH:5]([CH3:7])[CH3:6])[CH2:3][OH:4])=[O:31])[CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (S)-2-amino-3-methylbutan-1-ol (550 mg, 5.33 mmol) and (3S,5R,6R)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyltetrahydro-2H-pyran-2-one (Example 261, Step H, 2nd compound, 500 mg, 1.332 mmol) was heated to 100° C. for 24 h. After cooling to room temperature, the residue was dissolved in ethyl acetate and washed 3× with 1N HCl (5 mL) followed by sat. aq. NaCl solution (5 mL). The organic phase was dried over MgSO4, filtered, and the filtrate was concentrated to afford the title compound.

Workup

temperatureAfter cooling to room temperature
washwashed 3× with 1N HCl (5 mL)
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-7f044a8bc4f348719acd7fa7e051fc18
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569341B2

Reaction notes

Loading…