Triethylamine → HCID 59161011, compound

HRID 1873571Notes

Reaction equation

[Si:1]([O:18][CH2:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([O:29][CH2:30][C:31](Cl)=[O:32])(=[O:28])[CH3:27].C(N(CC)CC)C>ClCCl>[C:26]([O:29][CH2:30][C:31]([N:23]1[CH2:24][CH2:25][CH:20]([CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:15])[CH3:16])([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:21][CH2:22]1)=[O:32])(=[O:28])[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

5 g of the crude product from Example 20A are suspended in 24 ml of dichloromethane and cooled to 0° C. 1.88 g (13.79 mmol) of acetoxyacetyl chloride and 5.9 ml (42.42 mmol) of triethylamine are added. The reaction mixture is stirred at RT for 8 h. After addition of 25 ml of dichloromethane the mixture is washed once with 10 ml of water and once with 10 ml of saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate. After removal of the solvent on a rotary evaporator the residue is purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 20:1→1:1).

Workup

washis washed once with 10 ml of water and once with 10 ml of saturated aqueous sodium chloride solution
dry with materialThe organic phase is dried over magnesium sulfate
customAfter removal of the solvent
customon a rotary evaporator the residue
customis purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 20:1→1:1)

Sources & evidence

ORD record: ord-7c2f2eb20d1e49c48d9b964afb7071e4
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304412B2

Reaction notes

Loading…