Hexane → HCID 10024491, compound

HRID 654311Notes

Reaction equation

HRID 654311 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:10](OS(C)(=O)=O)/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N[C@@H]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C@@H](OS(C)(=O)=O)/C=C/C(OC)=O)=O)(C)(C)C.CCCCCC>C(OCC)(=O)C>[CH2:50]([C@@H:12](/[CH:11]=[CH:10]/[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:13]([O:15][CH3:16])=[O:14])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

5

Reactant 3

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

Product 1

HCID 10024491HCID 10024491, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using the procedure of Example 8 but replacing the resultant compound of Example 7 with the resultant compound of Example 14 provided, after silica gel chromatography using 6:1 hexane:ethyl acetate, the desired compound (m.p. 84°-85° C., R 0.73, 2:1 hexane:ethyl acetate) in 90% yield. 1H NMR (CDCl3) 1.41 s, 9 H), 2.7-2.8 (m, 3 H), 3.01 (dd, J=14, 8 Hz, 1 H), 3.26 (q, J=7 Hz, 1 H), 3.61 (s, 3 H), 4.37 (m, 2 H), 5.42 (br d, 1 H), 5.56 (dd, J=15, 8 Hz, 1 H), 7.03-7.12 (m, 4 H), 7.2-7.3 (m, 6 H).

Workup

  1. customprovided

Sources & evidence

ORD record
ord-8c699faea47444e18d4e7eb731006606
Source dataset
uspto-grants-1992_07
Patent number
US05130468

Reaction notes

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