Ethyl Acetate → HCID 86681597, compound

HRID 1912368Notes

Reaction equation

HRID 1912368 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:17](=[O:21])[C:18]([CH3:20])=[CH2:19])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCOC(C)=O>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@H:17]([OH:21])[C:18]([CH3:20])=[CH2:19])=[CH:11][CH:10]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86681596HCID 86681596, compound

Product 1

HCID 86681597HCID 86681597, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

This compound was prepared from ketone 67 (0.70 g, 1.85 mmol) in a synthetic procedure similar to that for compound and obtained after column chromatography (10%->25% EtOAc/PE) as a colorless oil (yield: 0.71 g, 1.85 mmol, quant.). 1H NMR (400 MHz, CDCl3): δ=7.32-7.18 (m, 7H), 7.04 (d, J=8.15 Hz, 2H), 6.77 (s, 1H), 5.17 (d, J=9.01 Hz, 1H), 5.05-4.91 (m, 4H), 4.14-4.10 (m, 1H), 4.05-3.97 (m, 1H), 3.01 (s, 1H), 2.86-2.78 (m, 1H), 2.64 (dd, J=14.18, 9.64 Hz, 1H), 1.76 (s, 3H), 1.50 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3): δ=156.03, 152.82, 144.45, 136.48, 136.33, 132.60, 129.65, 128.24, 127.79, 127.70, 118.49, 112.28, 80.17, 76.61, 66.37, 54.06, 33.46, 28.20, 18.71 ppm. [α]D23=−13.8 (c=1, CHCl3). HRMS: calcd. for C25H32N2O5 441.23840 [M+H]+. found 441.23843.

Sources & evidence

ORD record
ord-b552da0f8f8e415781b444fee2e93e44
Source dataset
uspto-grants-2013_12
Patent number
US08609610B2

Reaction notes

Loading…