Hexane → HCID 131717463, compound

HRID 654309Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:10]([O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[CH:11]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCCCC.[C:33]([O:36][CH2:37]C)(=[O:35])[CH3:34]>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@@H:10]([O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)/[CH:11]=[CH:34]/[C:33]([O:36][CH3:37])=[O:35])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 8058Hexane

HCID 8857Ethyl Acetate

HCID 57055042HCID 57055042, compound

Product 1

HCID 131717463HCID 131717463, compoundYield 69%

Procedure

Using the procedure of Example 5 with the resultant compound of Example 11 provided, after silica gel chromatography using 6:1 hexane:ethyl acetate, the desired compound (Rf 0.55, 7:3 hexane:ethyl acetate) in 69% yield. 1H NMR spectrum showed a 1:1 mixture of diastereomers. Mass spectrum: (M+H)+ =420.

Workup

customprovided

Sources & evidence

ORD record: ord-860a1cc0ea534ae6b54d7372636a380b
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05130468

Reaction notes

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