2,2-Dimethoxypropane → HCID 15550447, compound
Reaction equation
[OH:1][C@@H:2]1[C@H:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:4][C:3]1=[O:12].[CH3:13][O:14][C:15](OC)([CH3:17])[CH3:16].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CN(C)C=O>[CH3:13][O:14][C:15]([CH3:17])([O:1][C@@H:2]1[C@H:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:4][C:3]1=[O:12])[CH3:16]Participants
Conditions
- Temperature
- 0 °C
Procedure
A mixture of the title product of step (a) of Example 1 (79.7 mg, 0.488 mmoles), dimethoxy propane (0.3 ml, 2.44 mmol), PPTS (about 12 mg, 0.049 mmol) and dimethylformamide (2 ml) under argon were stirred for 3 hours at about 0° C. and then for 24 hours at about 4° C. The product obtained was extracted with ethyl acetate and worked up (diluted with 10 ml ethyl acetate, washed with 0.5 saturated aqueous NaHCO3; aqueous fraction extracted with 2×5 ml ethyl acetate; combined organic fractions were washed with 1×10 ml water, 10 ml saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated) to obtain quantitive yield of products, which was a 1:1.7 mixture of starting material and the title product (determined by TLC analysis).
Workup
- waitfor 24 hours at about 4° C
- customThe product obtained
- extractionwas extracted with ethyl acetate
- addition(diluted with 10 ml ethyl acetate, washed with 0.5 saturated aqueous NaHCO3; aqueous fraction extracted with 2×5 ml ethyl acetate; combined organic fractions were washed with 1×10 ml water, 10 ml saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated)
- customto obtain quantitive yield of products, which
- additiona 1:1.7 mixture of starting material
Sources & evidence
- ORD record
- ord-daba87a02a9046bcba9f2503cbf2a057
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06310201B1
Reaction notes
Loading…