Ethyl Acetate → HCID 77750102, compound
Reaction equation
CC(C[AlH]CC(C)C)C.[OH:10][CH2:11][CH2:12][CH:13]1[CH2:17][CH:16]([N:18]2[C:22]3[N:23]=[C:24]([S:37][CH2:38]CC)[N:25]=[C:26]([NH:27][CH:28]4[CH2:30][CH:29]4[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:21]=3[N:20]=[N:19]2)[CH:15]([OH:41])[CH:14]1[OH:42].C(OCC)(=O)C>C1(C)C=CC=CC=1>[OH:10][CH2:11][CH2:12][CH:13]1[CH2:17][CH:16]([N:18]2[C:22]3[N:23]=[C:24]([S:37][CH3:38])[N:25]=[C:26]([NH:27][CH:28]4[CH2:30][CH:29]4[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:21]=3[N:20]=[N:19]2)[CH:15]([OH:41])[CH:14]1[OH:42]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 4 °C
Procedure
DIBAL-H® (1.5M solution in toluene, 20 ml) was added to an ice-cooled solution of the product of Example 11, step a) (2.00 g) in toluene (30 ml) and the solution stirred at this temperature for 30 minutes before adding ethyl acetate (2 ml). The solution was washed with water and concentrated. The residue (1.8 g) was taken into ethanol and cooled to 4° C. before adding 3-chloroperoxybenzoic acid (50-55%, 2.5 g) and allowing the reaction to stir at room temperature for 18 hours. The solution was washed with aqueous sodium metabisulfite solution (3×10 ml) then dried and concentrated. Purification (SiO2, ether:isohexane, 80:20, as eluent) afforded the subtitle compound (1.8 g).
Workup
- washThe solution was washed with water
- concentrationconcentrated
- additionbefore adding 3-chloroperoxybenzoic acid (50-55%, 2.5 g)
- customthe reaction
- stirringto stir at room temperature for 18 hours
- washThe solution was washed with aqueous sodium metabisulfite solution (3×10 ml)
- customthen dried
- concentrationconcentrated
- customPurification (SiO2, ether:isohexane, 80:20, as eluent)
Sources & evidence
- ORD record
- ord-6459a5ea89e6477eb3e9a39ac82593e2
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06251910B1
Reaction notes
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