Acetic Anhydride → HCID 91274444, compound

HRID 2366508Notes

Reaction equation

HRID 2366508 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([O:11][C@@H:12]1[C@@H:24]([N:25]=[N+:26]=[N-:27])[C@@H:23]([OH:28])[C@@H:22]([CH2:29][OH:30])[O:21][C@H:13]1[S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:10])[CH3:9].CCCCCCC.[CH3:38][CH2:39][O:40]C(C)=O>N1C=CC=CC=1>[C:8]([O:11][C@@H:12]1[C@@H:24]([N:25]=[N+:26]=[N-:27])[C@@H:23]([O:28][C:1](=[O:3])[CH3:2])[C@@H:22]([CH2:29][O:30][C:39](=[O:40])[CH3:38])[O:21][C@H:13]1[S:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 8900HeptaneHCID 91614006HCID 91614006, compound

Product 1

HCID 91274444HCID 91274444, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (30 mL) was added to a solution of compound 6 (373 mg, 1.1 mmol) in dry pyridine (30 mL). The reaction was monitored by TLC (heptane:EtOAc, 1:1) and when it was complete, it was concentrated under reduced pressure. 1H NMR in CDCl3 δ 7.54-7.51 (m, 2H, Ar), 7.35-7.30 (m, 3H, Ar), 5.46 (dd, 1H, H-4), 5.23 (t, 1H, H-2), 4.73 (d, 1H, H-1), 4.15 (d, 2H, H-6, H-6), 3.94 (dt, 1H, H-5), 3.68 (dd, 1H, H-3), 2.18 (s, 3H, OAc), 2.15 (s, 3H, OAc), 2.06 (s, 3H, OAc).

Workup

  1. concentrationit was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b08b89013d654695af701221828fe4e5
Source dataset
uspto-grants-2014_04
Patent number
US08697862B2

Reaction notes

Loading…