Pyridine → (+)-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid phenyl ester

HRID 985811Notes

Reaction equation

HRID 985811 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[C:7]1[C:15]2[S:14][C:13]([NH2:16])=[N:12][C:11]=2[C:10]([O:17][CH3:18])=[CH:9][CH:8]=1.N1C=CC=CC=1.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27].C(=O)(O)[O-].[Na+]>ClCCl>[C:29]1([O:28][C:26](=[O:27])[NH:16][C:13]2[S:14][C:15]3[C:7]([CH:2]4[CH2:3][O:4][CH2:5][CH2:6][O:1]4)=[CH:8][CH:9]=[C:10]([O:17][CH3:18])[C:11]=3[N:12]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 22507697(+)-7-[1,4)Dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine

Product 1

HCID 20769454(+)-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid phenyl esterYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 450 mg (1.69 mmol) (+)-7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine and 0.41 ml (5.07 mmol) pyridine in 10 ml dichloromethane at 0° C. was added 0.28 ml (2.20 mmol) phenyl chloroformate and stirring continued at room temperature for 16 h. The reaction mixture was then poured into saturated aqueous sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/1 acetone/heptane) followed by trituration in ether and hexane afforded 630 mg (96%) (+)-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid phenyl ester as a white solid. [α]D20=+13.6° (c=0.32, CHCl3), ES-MS m/e (%):387 (M+H+, 100).

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-275a909c1f334a76b46ea22496247ece
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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