Methanol → 4-hydroxy-N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidin-4-yl]-3,3-dimethyl-1-butanesulfonamide

HRID 397263Notes

Reaction equation

HRID 397263 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][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:18])=[O:17])[C:4]=1[O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH3:33].C[OH:35]>>[OH:35][CH2:22][C:21]([CH3:24])([CH3:23])[CH2:20][CH2:19][S:16]([NH:15][C:5]1[C:4]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])=[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 22999702N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide

Product 1

HCID 229997174-hydroxy-N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidin-4-yl]-3,3-dimethyl-1-butanesulfonamide

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 six 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]-3,3-dimethyl-1-butanesulfonamide (Preparation 1) 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, 430 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, 430 mg

Sources & evidence

ORD record
ord-cd99e483e2284ba09a7fa81b1de0ee25
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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