HCID 67003850, compound → HCID 16720388, compound

HRID 1045243Notes

Reaction equation

HRID 1045243 reaction equation
C(O[C@H](CCCCCCCCCC(C)C)CC(O)=O)C1C=CC=CC=1.[CH2:26]([O:33][C@H:34]([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH:60]([CH3:62])[CH3:61])[CH2:35][C:36]([O:38]CC(C1C=CC(Br)=CC=1)=O)=[O:37])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>[Zn]>[CH2:26]([O:33][C@H:34]([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH:60]([CH3:62])[CH3:61])[CH2:35][C:36]([OH:38])=[O:37])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 67003850HCID 67003850, compoundHCID 86644997HCID 86644997, compound

Product 1

HCID 16720388HCID 16720388, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

In a manner similar to the synthesis of 107, compound 119 (350 mg, 0.611 mmol) was treated with zinc (<10 micron, 397 mg, 6.11 mmol) to afford 108 as an amorphous solid (207 mg, 97%). Rf=0.45 (toluene/ethyl acetate, 3/1, v/v); [α]25D=−2.5° (c=1.0, CHCl3); 1H NMR (300 MHz, CDCl3): δ 7.34-7.26 (m, 5H, aromatic), 4.57 (s, 2H, CH2Ph), 3.87 (m, 1H, H-3), 2.64 (dd, 1H, J2a,2b=15.6 Hz, J2a,3=6.9 Hz, H-2a), 2.55 (dd, 1H, J2a,2b=15.6 Hz, J2b,3=5.1 Hz, H-2b), 1.68-1.38 (m, 3H, H-4, H-15), 1.26-1.14 [m, 20H, H-(5-14)], 0.86 (d, 6H, J15,16=6.9 Hz, H-16); 13C NMR (75 MHz, CDCl3): δ 176.95 (C═O), 138.08-127.71 (aromatic), 75.71 (C-3), 71.53 (CH2Ph), 39.47 (C-2), 39.05 (C-12), 34.12 (C-4), 22.65 (C-14). HR MS (m/z) calculated for C24H40O3 [M+Na]+, 399.2870; found, 399.2552.

Sources & evidence

ORD record
ord-9473bfcff07048b5ba24414b93080f70
Source dataset
uspto-grants-2013_10
Patent number
US08563523B2

Reaction notes

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