Dichloromethane → Dichloromethane methanol ammonium hydroxide

A stirred mixture of 53 (about 2.07 mmol), triethylamine (2.3 ml, 16.6 mmol), CH2Cl2 (21 ml) and THF (21 ml) was treated with acetyl chloride (270 mg, 3.11 mmol) and kept at ambient temperature for 18 h. It was concentrated in vacuo and the residue was mixed with saturated NaHCO3 and extracted with CH2Cl2. The extract was dried (MgSO4) and concentrated. Chromatography of the residue on silica gel with mixtures of MeOH—NH4OH—CH2Cl2 containing 2.5–10% MeOH and 0.25–1% NH4OH gave the product which was crystallized from EtOH to give 835 mg of 55: mp 178–179° C.; 1H NMR [300 MHz, (CD3)2SO] δ 1.82 (s, 3H), 2.34 (m, 4H), 2.73 (t, 2H), 2.90 3.00 (s, s, 4H), 3.22 (t, 2H), 3.39 (t, 2H), 3.55 (m, 8H), 3.66 (m, 3H), 4.07 (t, 1H), 4.69 (m, 1H), 7.07 (t, 1H), 7.17 (dd, 1H), 7.46 (m, 3H), 7.93 (d, 2H), 8.21 (t, 1H),

1. concentrationIt was concentrated in vacuo
2. additionthe residue was mixed with saturated NaHCO3
3. extractionextracted with CH2Cl2
4. dry with materialThe extract was dried (MgSO4)
5. concentrationconcentrated

ORD record

ord-fd40c2f92fdc479aa7a9aacbc3f3c356

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141570B2