Ethyl Acetate → HCID 178499569, compound

HRID 430722Notes

Reaction equation

HRID 430722 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C@:10]([CH3:17])([CH:12]([O:15][CH3:16])[O:13][CH3:14])[C@@H:9]([OH:18])[C@H:8]([NH2:19])[C:7]=2[CH:20]=1)#[N:2].[Na].[C:22]([NH:24][C:25]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)=S)#[N:23].Cl.CN(C)CCCCCN=C=N.C(OCC)(=O)C>CN(C=O)C>[C:22]([N:24]=[C:25]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[NH:19][C@@H:8]1[C:7]2[CH:20]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[O:11][C@:10]([CH3:17])([CH:12]([O:15][CH3:16])[O:13][CH3:14])[C@H:9]1[OH:18])#[N:23]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 574828161-(3-Dimethylaminopropyl)-2-ethylcarbodiimide hydrochlorideHCID 70237354HCID 70237354, compoundHCID 86757615n-Cyano-n'-(4-chlorophenyl)thiourea sodium salt

Product 1

HCID 178499569HCID 178499569, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg of (2S,3S,4R)-6-cyano-2-methyl-2-dimethoxymethyl-3-hydroxy-4-amino-3,4-dihydro-2H-1-benzopyran prepared in the preparation example 6 is dissolved in 3 ml of DMF, were added 92 mg of N-cyano-N′-(4-chlorophenyl)thiourea sodium salt and 89 mg of 1-[3-(dimethylamino)propyl]-2-ethylcarbodiimide hydrochloride. The reaction mixture was stirred for 6 hours at room temperature, and extracted with 30 ml of ethyl acetate after acidifying the mixture by adding 5 ml of 1N HCl. The organic Layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by siLica gel chromatography (n-hexane:ethyl acetate=1:1 to afford 70 mg (yield: 43%) of the desired compound Of (2S,3R,4S) stereochemistry.

Workup

  1. extractionextracted with 30 ml of ethyl acetate
  2. additionby adding 5 ml of 1N HCl
  3. dry with materialThe organic Layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by siLica gel chromatography (n-hexane

Sources & evidence

ORD record
ord-33a109aa14e64d0499459d97a84a6ae8
Source dataset
uspto-grants-2001_11
Patent number
US06323238B1

Reaction notes

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