Hexane → HCID 131717464, compound

HRID 654313Notes

Reaction equation

HRID 654313 reaction equation
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]([O:13][C:14]([NH:16][C@@H:17]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@H:18](OS(C)(=O)=O)/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(OC(N[C@@H](CC1C=CC=CC=1)[C@@H](OS(C)(=O)=O)/C=C/C(OC)=O)=O)(C)(C)C.CCCCCC>C(OCC)(=O)C>[C:9]([O:13][C:14]([NH:16][C@@H:17]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)/[CH:18]=[CH:19]/[C@H:20]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:21]([O:23][CH3:24])=[O:22])=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 8058HexaneHCID 14656852HCID 14656852, compoundHCID 14656853HCID 14656853, compoundHCID 178478990HCID 178478990, compound

Product 1

HCID 131717464HCID 131717464, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using the procedure of Example 8 but replacing benzylmagnesium chloride with cyclohexylmagnesium chloride (2.0M solution in ether) and replacing the resultant compound of Example 7 with the resultant compound of Example 14 provided, after chromatography on silica gel using 6:1 hexane:ethyl acetate, the desired compound (Rf 0.65, 2:1 hexane:ethyl acetate) in 82% yield. 1H NMR (CDCl3) δ 0.6-1.7 (br envelope, 11 H), 1.41 (s, 9 H), 2.69 (m, 1 H), 2.75 (dd, J=14, 7 Hz, 1 H), 2.89 (dd, J=14, 5 Hz, 1 H), 3.66 (s, 3 H), 4.41 (m, 2 H), 5.44 (AA', 2 H), 7.1-7.3 (m, 5 H). Mass spectrum: (M+H)+ =402.

Workup

  1. customprovided

Sources & evidence

ORD record
ord-4edf24d48b7a41bfb9a467a87c697765
Source dataset
uspto-grants-1992_07
Patent number
US05130468

Reaction notes

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