Ethyl Acetate → HCID 22844978, compound

HRID 654314Notes

Reaction equation

HRID 654314 reaction equation
[CH2:1]([Mg]Cl)CC.C(OC(N[C@@H](CC1C=CC=CC=1)[C@H](OS(C)(=O)=O)/C=C/C(OC)=O)=O)(C)(C)C.[C:34]([O:38][C:39]([NH:41][C@@H:42]([CH2:56][CH:57]1[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]1)[C@@H:43](OS(C)(=O)=O)/[CH:44]=[CH:45]/[C:46]([O:48][CH2:49][CH3:50])=[O:47])=[O:40])([CH3:37])([CH3:36])[CH3:35].C(OCC)(=O)C>CCCCCC>[C:34]([O:38][C:39]([NH:41][C@H:42](/[CH:43]=[CH:44]/[C@@H:45]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[CH3:1])[CH2:56][CH:57]1[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]1)=[O:40])([CH3:37])([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14656853HCID 14656853, compoundHCID 131717465HCID 131717465, compoundHCID 178455855HCID 178455855, compound

Product 1

HCID 22844978HCID 22844978, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Using the procedure of Example 8 but replacing benzylmagnesium chloride with n-propylmagnesium chloride and replacing the resultant compound of Example 7 with the resultant compound of Example 27 provided, after silica gel chromatography using 15% ethyl acetate in hexane, the desired compound (Rf 0.35, 4:1 hexane:ethyl acetate) in 6% yield. 1H NMR (CDCl3) δ 0.8-1.0 (m, 2 H), 0.90 (t, J=7 Hz, 3 H), 1.1-1.8 (br envelope, 15 H), 1.43 (s, 9 H), 2.97 (q, J=8 Hz, 1 H), 4.12 (q, J=7 Hz, 2 H), 4.33 (m, H), 5.43 (br d, 1 H), 5.56 (dd, J=16, 9 Hz, 1 H). 13C NMR (CDCl3, ppm) 13.77, 14.22, 20.24, 26.25, 26.30, 26.53, 28.38 (3 C), 33.16, 34.19, 34.65, 43.31, 48.72, 49.46, 49.50, 60.43, 127.89, 133.83, 174.33 . Mass spectrum: (M+H)+ =382.

Workup

  1. customprovided

Sources & evidence

ORD record
ord-6248ea6982024514a8af0e3da1a3d38e
Source dataset
uspto-grants-1992_07
Patent number
US05130468

Reaction notes

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