Potassium tert-butoxide → HCID 178437376, compound

HRID 925979Notes

Reaction equation

HRID 925979 reaction equation
CC(C)([O-])C.[K+].[C:7]([C:10]1[C:15]([NH:16][C:17]([C:19]2[S:20][CH:21]=[C:22]([CH:24]=[CH2:25])[N:23]=2)=O)=[C:14]([Cl:26])[C:13]([O:27][CH3:28])=[CH:12][CH:11]=1)(=[O:9])[CH3:8]>C(O)(C)(C)C.C(OCC)C>[Cl:26][C:14]1[C:13]([O:27][CH3:28])=[CH:12][CH:11]=[C:10]2[C:15]=1[N:16]=[C:17]([C:19]1[S:20][CH:21]=[C:22]([CH:24]=[CH2:25])[N:23]=1)[CH:8]=[C:7]2[OH:9]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 57816686HCID 57816686, compound

Product 1

HCID 178437376HCID 178437376, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

Potassium tert-butoxide (2.13 g, 2.2 eq.) was added to a suspension of compound 272 (2.91 g, 1 eq.) in tert-butanol (30 mL). The reaction mixture was heated to 100° C. for 5 hrs. After one night at room temperature, the mixture was diluted with diethyl ether and the precipitate filtered, washed with diethyl ether, and solubilized in water. The pH was adjusted to 6-7 by addition of 1N HCl and the precipitate was filtered, washed with water, and triturated with diethyl ether to yield compound 273 in 73% yield. 1H NMR (CDCl3, 400 MHz): δ (ppm) 4.06 (s, 3H), 5.54 (d, J=10.82 Hz, 1H), 6.25 (d, J=17.31 Hz, 1H), 6.74 (s, 1H), 6.79 (dd, J=17.31 and 10.82 Hz, 1H), 7.06 (d, J=9.10 Hz, 1H), 7.32 (s, 1H), 8.28 (d, J=9.10 Hz, 1H), 9.97 (br s, 1H).

Workup

  1. waitAfter one night at room temperature
  2. filtrationthe precipitate filtered
  3. washwashed with diethyl ether
  4. additionThe pH was adjusted to 6-7 by addition of 1N HCl
  5. filtrationthe precipitate was filtered
  6. washwashed with water
  7. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-1e9ef63946bd4c8fbc71793ec60bcfd5
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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