Methanol → HCID 86758073, compound

HRID 1935425Notes

Reaction equation

HRID 1935425 reaction equation
O1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:29][CH2:30][CH2:31][O:32][C:33]4[N:38]=[CH:37][C:36]([Br:39])=[CH:35][N:34]=4)=[N:12][O:13][C:14]=3[NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22](C(C)(C)C)=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:9][C:4]=2[O:3]C1.[CH3:40][OH:41]>>[O:41]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:29][CH2:30][CH2:31][O:32][C:33]4[N:38]=[CH:37][C:36]([Br:39])=[CH:35][N:34]=4)=[N:12][O:13][C:14]=3[NH:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:10]([CH3:11])([CH3:8])[CH2:14][OH:13])(=[O:17])=[O:18])=[CH:9][C:4]=2[O:3][CH2:40]1

Participants

3

Reactant 2

HCID 887MethanolHCID 10211171HCID 10211171, compound

Product 1

HCID 86758073HCID 86758073, compound

Procedure

Amycolata autotrophica ATCC35203 maintained on a quarter strength ATCC172 agar slope was inoculated as a loopful of spores into a 300 ml Erlenmeyer flasks each containing 50 ml of MY inoculum medium. This was allowed to incubate for 2 days at 28° C., 200 rpm on an Infors Multitron™ Shaker with 1 ″ throw. Two mLs of this inoculum was then transferred to each of twenty 300 ml Erlenmeyer flask containing 50 ml of MY production medium and incubated under the same conditions for a further 24 hours. At this point 5 mg of N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-5-isoxazolyl)-4-(tert-butyl)benzene-sulfonamide (Example 2) dissolved in 0.5 mL of methanol was added to each of the flasks and the fermentation allowed to continue under the same conditions for a further 144 hours. Each flask was then extracted with 200 mls of ethyl acetate and the combined ethyl acetate solubles concentrated to dryness to give a gum solid.

Workup

  1. temperatureAmycolata autotrophica ATCC35203 maintained on a quarter strength ATCC172 agar slope
  2. additioncontaining 50 ml of MY production medium
  3. waitincubated under the same conditions for a further 24 hours
  4. additionwas added to each of the flasks
  5. waitto continue under the same conditions for a further 144 hours
  6. extractionEach flask was then extracted with 200 mls of ethyl acetate
  7. concentrationthe combined ethyl acetate solubles concentrated to dryness
  8. customto give a gum solid

Sources & evidence

ORD record
ord-af55adb4107042e7902917803e9b78e7
Source dataset
uspto-grants-2002_05
Patent number
US06387915B2

Reaction notes

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