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Tetrahydrofuran → 4-(4-But-2-ynyloxy-phenylsulfanylmethyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester

HRID 353552
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HRID 353552 반응식
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][C:14]2([C:27]([O:29]CC)=[O:28])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[OH-].[Na+].C1COCC1>CO>[C:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][C:14]([CH2:13][S:12][C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:7][CH:8]=2)([C:27]([OH:29])=[O:28])[CH2:15][CH2:16]1)=[O:21])([CH3:26])([CH3:25])[CH3:24]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 697267481-(Tert-butyl) 4-ethyl 4-({[4-(2-butynyloxy)phenyl]sulfanyl}methyl)-1,4-piperidinedicarboxylate

생성물 1

HCID 542579274-(4-But-2-ynyloxy-phenylsulfanylmethyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester수율 893.4%

시약·촉매·용매 1

HCID 887Methanol
용매

실험 절차

A mixture of 0.288 g (0.0643 mmol) of 1-(tert-butyl) 4-ethyl 4-({[4-(2-butynyloxy) phenyl]sulfanyl}methyl)-1,4-piperidinedicarboxylate, 3.25 mL of 1N NaOH 3.25 mL of THF and 3.25 mL of MeOH was heated to reflux for 3 h. The organics were removed and the residue was diluted with H2O, acidified and extracted with EtOAC. The organics were washed with H2O, brine, dried over mgSO4, filtered and concentrated in vacuo to provide 0.241 g (89%) of the desired product as an off white gum. Electrospray Mass Spec: 464.3 (M+FA−H)+.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customThe organics were removed
  4. additionthe residue was diluted with H2O
  5. extractionextracted with EtOAC
  6. washThe organics were washed with H2O, brine
  7. customdried over mgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5cab747bb19c4646b5d736881b7e6929
출처 데이터셋
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06753337B2

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