Water → Dimethylcarbamic acid 3-{3-((tert-butoxycarbonyl)aminosulfonyl)aminobenzyl}-6-chloro-4-fluoromethyl-2-oxo-2H-1-benzopyran-7-yl ester

HRID 1046788Notes

Reaction equation

HRID 1046788 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([N-:15][S:16](N1C=CC(=[N+](C)C)C=C1)(=[O:18])=[O:17])=[O:14])([CH3:11])([CH3:10])[CH3:9].[NH2:28][C:29]1[CH:30]=[C:31]([CH:53]=[CH:54][CH:55]=1)[CH2:32][C:33]1[C:34](=[O:52])[O:35][C:36]2[CH:44]=[C:43]([O:45][C:46](=[O:50])[N:47]([CH3:49])[CH3:48])[C:42]([Cl:51])=[CH:41][C:37]=2[C:38]=1[CH2:39][F:40].O>ClCCl>[C:8]([O:12][C:13]([NH:15][S:16]([NH:28][C:29]1[CH:30]=[C:31]([CH:53]=[CH:54][CH:55]=1)[CH2:32][C:33]1[C:34](=[O:52])[O:35][C:36]2[CH:44]=[C:43]([O:45][C:46](=[O:50])[N:47]([CH3:49])[CH3:48])[C:42]([Cl:51])=[CH:41][C:37]=2[C:38]=1[CH2:39][F:40])(=[O:18])=[O:17])=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 59139328dimethylcarbamic acid 3-(3-aminobenzyl)-6-chloro-4-fluoromethyl-2-oxo-2H-1-benzopyran-7-yl esterHCID 178482962HCID 178482962, compound

Product 1

HCID 59139501Dimethylcarbamic acid 3-{3-((tert-butoxycarbonyl)aminosulfonyl)aminobenzyl}-6-chloro-4-fluoromethyl-2-oxo-2H-1-benzopyran-7-yl esterYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (34 μL, 0.25 mmol) and N-(tert-butoxycarbonyl)-N-{4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl}azanide (49 mg, 0.16 mmol) were added in series to a solution of dimethylcarbamic acid 3-(3-aminobenzyl)-6-chloro-4-fluoromethyl-2-oxo-2H-1-benzopyran-7-yl ester (compound 1h-1-3F) (33 mg, 0.082 mmol) in anhydrous dichloromethane (1.0 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate. A crude solid was then obtained by vacuum concentration, and purified by preparative TLC (ethyl acetate:hexane=1:2) to yield the title compound (30 mg, 63%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. customA crude solid was then obtained by vacuum concentration
  6. custompurified by preparative TLC (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-c97dcd8bf5a34a6eb21aa7e002a3f0c2
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

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