Sodium → HCID 58573518, compound

HRID 932155Notes

Reaction equation

[CH2:1]([C@@:4]1([CH3:30])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:27][CH3:28])[CH:25]=O)[C:5]1=[O:29])[CH:2]=[CH2:3].Cl.[NH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38]CC)=O.[Na]>C(O)(=O)C.C1COCC1.CO>[CH2:1]([C@@:4]1([CH3:30])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:27][CH3:28])[CH2:25][N:32]2[CH2:33][CH2:34][CH2:35][C:36]2=[O:38])[C:5]1=[O:29])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanal (84 mg, 0.189 mmol; Example 91, Step C), ethyl 4-aminobutyrate hydrochloride (127 mg, 0.756 mmol) and acetic acid (3 drops) in DCE/MeOH (3/1, 4.0 mL) was added sodium triacetoxyhydroborate (200 mg, 0.945 mmol) at 25° C. After being stirred at 25° C. for 18 h, the reaction was quenched by adding ice-cold saturated aqueous NaHCO3 solution and was extracted with DCM. The combined organic layers were washed (1×sat. aq. NaCl solution) and concentrated under reduced pressure. The residue was purified by reverse phase preparatory HPLC (acetonitrile in water with 0.1% TFA, gradient elution) to give the title compound as a white solid.

Workup

customthe reaction was quenched
additionby adding ice-cold saturated aqueous NaHCO3 solution
extractionwas extracted with DCM
washThe combined organic layers were washed (1×sat. aq. NaCl solution)
concentrationconcentrated under reduced pressure
customThe residue was purified by reverse phase preparatory HPLC (acetonitrile in water with 0.1% TFA, gradient elution)

Sources & evidence

ORD record: ord-9dca27599b46455fafa47a4dc71787e0
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296736B2

Reaction notes

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