Sodium Hydroxide → 6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylic acid

HRID 1630318ノート

反応式

HRID 1630318 の反応式
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:37])=[N:14][C:15]2[N:16]([N:29]=[C:30]([C:32]([O:34]CC)=[O:33])[CH:31]=2)[C:17]=1[C:18]1[CH:27]=[CH:26][C:21]2[O:22][CH2:23][CH2:24][NH:25][C:20]=2[C:19]=1[Cl:28])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:37])=[N:14][C:15]2[N:16]([N:29]=[C:30]([C:32]([OH:34])=[O:33])[CH:31]=2)[C:17]=1[C:18]1[CH:27]=[CH:26][C:21]2[O:22][CH2:23][CH2:24][NH:25][C:20]=2[C:19]=1[Cl:28])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 71258189Ethyl 6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate

生成物 1

HCID 712592426-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylic acid収率 77.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of ethyl 6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (315 mg, 0.593 mmol) in EtOH (6 mL) was added 1N NaOH (0.712 mL, 0.712 mmol) and the resulting mixture was stirred at room temp for 4 h. A this point LCMS indicated completion of reaction. Then, the reaction mixture was concentrated and the residue diluted with water (3 mL), acidified with 1N HCl, extracted with ethyl acetate (25 mL), washed with brine (10 mL), dried (Na2SO4), filtered and concentrated to afford 6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylic acid (230 mg, 0.457 mmol, 77% yield) as off-white solid (approx 2:1 mixture of mono and di-acid) which was used as is in the next step without further purification. LCMS (M+H)=503.3.

後処理

  1. customcompletion of reaction
  2. concentrationThen, the reaction mixture was concentrated
  3. additionthe residue diluted with water (3 mL)
  4. extractionextracted with ethyl acetate (25 mL)
  5. washwashed with brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford

出典と根拠

ORDレコード
ord-7d8d6b6263974b0d978d83d14fbe588c
出典データセット
uspto-grants-2014_07
特許番号
US08791108B2

反応ノート

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