Propyl chloroformate → HCID 15508230, compound

HRID 394597Notes

Reaction equation

HRID 394597 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][CH3:7])=[O:3].[O:8]([C:18]1[CH:29]=[CH:28][C:21]2[C:22]([CH3:27])=[CH:23][C:24](=[O:26])[O:25][C:20]=2[CH:19]=1)[C@@H:9]1[S:17][CH2:16][C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]1[OH:11]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH2:5]([O:4][C:2]([O:11][C@@H:10]1[C@@H:12]([O:13][C:2]([O:4][CH2:5][CH2:6][CH3:7])=[O:3])[C@H:14]([O:15][C:2]([O:4][CH2:5][CH2:6][CH3:7])=[O:3])[CH2:16][S:17][C@H:9]1[O:8][C:18]1[CH:29]=[CH:28][C:21]2[C:22]([CH3:27])=[CH:23][C:24](=[O:26])[O:25][C:20]=2[CH:19]=1)=[O:3])[CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 7998Propyl chloroformate2×HCID 216385Odiparcil

Product 1

HCID 15508230HCID 15508230, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 100 mg (0.8.10−3 mol) of 4-dimethylaminopyridine in 12 ml of pyridine is prepared and 2.1 ml (18.7.10−3 mol) of propyl chloroformate are added at 0° C., followed by 1 g (3.1.10−3 mol) of 4-methyl-2-oxo-2H-1-benzopyran-7-yl 5-thio-β-D-xylopyranoside. The reaction mixture is stirred for 1 hour, a further 1 ml (8.9.10−3 mol) of propyl chloroformate is then added and stirring is continued for 1 hour. The mixture is then hydrolyzed in ice water and extracted with ethyl acetate. The organic phase is washed with dilute hydrochloric acid solution and then with water, dried and finally concentrated under reduced pressure. The residue is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (4/1; v/v) as the eluent. The pure product fraction is crystallized from an ethyl acetate/ diethyl ether mixture to give 1.13 g of the expected product in the form of a fine and light white solid (yield=63%).

Workup

  1. stirringstirring
  2. waitis continued for 1 hour
  3. extractionhydrolyzed in ice water and extracted with ethyl acetate
  4. washThe organic phase is washed with dilute hydrochloric acid solution
  5. dry with materialwith water, dried
  6. concentrationfinally concentrated under reduced pressure
  7. customThe residue is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (4/1; v/v) as the eluent
  8. customThe pure product fraction is crystallized from an ethyl acetate/ diethyl ether mixture

Sources & evidence

ORD record
ord-adc51eb79a68453cb97b49a817d4e065
Source dataset
uspto-grants-2003_08
Patent number
US06602899B1

Reaction notes

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