HCID 67003850, compound → HCID 86644998, compound

HRID 628201Notes

Reaction equation

HRID 628201 reaction equation
C(O[C@H](CCCCCCCCCC(C)C)CC(O)=O)C1C=CC=CC=1.BrC1C=CC([C@:33](CC=O)([CH:37]([O:52][C:53](=[O:69])[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH:49]([CH3:51])[CH3:50])[C:34]([O-:36])=[O:35])=CC=1>[Zn]>[C:53]([O:52][C@H:37]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH:49]([CH3:50])[CH3:51])[CH2:33][C:34]([OH:36])=[O:35])(=[O:69])[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68]

Participants

4

Reactant 2

HCID 67003850HCID 67003850, compoundHCID 86644999HCID 86644999, compound

Product 1

HCID 86644998HCID 86644998, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

In a manner similar to the synthesis of 107, compound 120 (500 mg, 0.666 mmol) was treated with zinc (<10 micron, 430 mg, 6.66 mmol) to afford 109 as an amorphous solid (335 mg, 96%). Rf=0.35 (toluene/ethyl acetate, 4/1, v/v); [α]25D=−0.6° (c=1.0, CHCl3); 1H NMR (300 MHz, CDCl3): δ 5.19 (m, 1H, H-3), 2.58 (m, 2H, H-2), 2.25 (t, 2H, J=7.5 Hz, H-2′), 1.60-1.43 (m, 5H, H-4, H-15, H-3′), 1.23-1.14 [m, 44H, H-(5-14), H-(4′-15′)], 0.85-0.83 (m, 9H, H-16, H-16′); 13C NMR (75 MHz, CDCl3): δ 176.24 (C═O), 173.27 (C═O), 69.95 (C-3). HR MS (m/z) calculated for C33H64O4 [M+Na]+, 547.4697. found, 547.5009.

Sources & evidence

ORD record
ord-bbe9bae045964f5d821877a4f237a4ff
Source dataset
uspto-grants-2016_04
Patent number
US09309276B2

Reaction notes

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