Toluene → HCID 178521050, compound
Reaction equation
N[C:2]1[NH:7][C:6]2=[C:8]([C@@H:11]3[NH:19][C@H:16]([CH2:17][OH:18])[C@@H:14]([OH:15])[C@H:12]3O)[CH:9]=[N:10][C:5]2=[C:4]([OH:20])[N:3]=1.CC(OC(N(C)C)N(C)C)(C)C.C1(C)C=CC=CC=1>CN(C)C=O>[OH:20][C:4]1[N:3]=[CH:2][NH:7][C:6]2=[C:8]([C@@H:11]3[NH:19][C@H:16]([CH2:17][OH:18])[C@@H:14]([OH:15])[CH2:12]3)[CH:9]=[N:10][C:5]=12Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 67.5 °C
Procedure
To a solution of the product from Example 1.2 (0.88 g) in N,N-dimethylformamide (5 ml) was added tert-butoxy bis(dimethylamine)methane (1.5 ml) and the solution was heated at 65-70° C. for 1 h. Toluene (20 ml) was added and the solution was washed (×3) with water, dried and concentrated to dryness. The residue was dissolved in tetrahydrofuran/acetic acid/water (1:1:1 v/v/v, 40 ml) at room temperature. After 1.5 h chloroform (50 ml) was added and the mixture was washed with water (×2), aqueous sodium bicarbonate, and then dried and evaporated to dryness. Chromatography of the residue gave (1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (3) (0.68 g).
Workup
- washthe solution was washed (×3) with water
- customdried
- concentrationconcentrated to dryness
- dissolutionThe residue was dissolved in tetrahydrofuran/acetic acid/water (1:1:1 v/v/v, 40 ml) at room temperature
- additionAfter 1.5 h chloroform (50 ml) was added
- washthe mixture was washed with water (×2), aqueous sodium bicarbonate
- customdried
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-b6600e31d00b44a3bbd5a6e27a57e53e
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06228847B1
Reaction notes
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