Methanol → 5-hydroxy-N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide

HRID 397264Notes

Reaction equation

HRID 397264 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:6]=[C:5]([NH:15][S:16]([CH2:19][CH2:20][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:18])=[O:17])[C:4]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34].C[OH:36]>>[OH:36][CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][CH2:20][CH2:19][S:16]([NH:15][C:5]1[C:4]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])=[C:3]([O:2][CH3:1])[N:8]=[C:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:6]=1)(=[O:17])=[O:18]

Participants

3

Reactant 2

HCID 887MethanolHCID 22999699N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide

Product 1

HCID 229997215-hydroxy-N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide

Procedure

Streptomyces rimosus subsp. rimosus ATCC10970 maintained on a quarter strength ATCC172 agar slope was inoculated as a loopful of spores into a 300 ml Erlenmeyer flask containing 50 ml of AS-7H inoculum medium. This was allowed to incubate for 2 days at 28° C., 200 rpm on an Infors Multitron Shaker with 1″ throw. 2 mls of this inoculum medium was then transferred to twenty 300 ml Erlenmeyer flask containing 50 ml of AP-5H production medium and incubated under the same conditions for a further 24 hours. At this point 4.5 mg of N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide (Preparation 3) 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 20 hours. The flask was then extracted with 200 mls of ethyl acetate and the combined ethyl acetate solubles concentrated to dryness to give a gum solid, 200 mg.

Workup

  1. temperaturerimosus ATCC10970 maintained on a quarter strength ATCC172 agar slope
  2. additioncontaining 50 ml of AS-7H inoculum medium
  3. additioncontaining 50 ml of AP-5H production medium
  4. waitincubated under the same conditions for a further 24 hours
  5. additionwas added to each of the flasks
  6. waitto continue under the same conditions for a further 20 hours
  7. extractionThe flask was then extracted with 200 mls of ethyl acetate
  8. concentrationthe combined ethyl acetate solubles concentrated to dryness
  9. customto give a gum solid, 200 mg

Sources & evidence

ORD record
ord-773bd47a861c47109361e2660a4ef394
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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