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Hydrochloric Acid → Benzyl (6-oxo-1-(2-oxoethyl)-2-phenyl-1,6-dihydropyrimidin-5-yl)carbamate

HRID 353335
ノート
印刷プレビュー

反応式

HRID 353335 の反応式
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:10](=[O:11])[C:9]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[CH:8][N:7]=[C:6]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>O1CCCC1>[CH2:16]([O:15][C:13]([NH:12][C:9]1[C:10](=[O:11])[N:5]([CH2:4][CH:3]=[O:2])[C:6]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:7][CH:8]=1)=[O:14])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 9866209[5-[(Benzyloxycarbonyl)amino]-2-phenyl-6-oxo-1,6-dihydro-1-pyrimidinyl]acetaldehyde dimethyl acetal

生成物 1

HCID 10361338Benzyl (6-oxo-1-(2-oxoethyl)-2-phenyl-1,6-dihydropyrimidin-5-yl)carbamate収率 102.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(EX-1D) A solution of [5-[(benzyloxycarbonyl)amino]-2-phenyl-6-oxo-1,6-dihydro-1-pyrimidinyl]acetaldehyde dimethyl acetal (17.24 g, 42.11 mmol) in 103.0 mL tetrahydrofuran was added 35.0 mL 1 N HCl. The resulting biphasic mixture was allowed to heated to reflux for 12 hours. The reaction mixture was allowed to cool to room temperature and the volatiles were removed under vacuum. The resulting residue was diluted.with water (200 mL) and the pH was adjusted to 7 by addition of solid NaHCO3. The resulting emulsion was extracted with dichloromethane (4×150 mL). The combined organic solutions were washed with water 1×200 mL), dried (MgSO4), filtered, and concentrated to give 15.74 g crude [5-[(benzyloxycarbonyl)amino]-2-phenyl-6-oxo-1,6-dihydro-1-pyrimidinyl]acetaldehyde.

後処理

  1. temperatureto heated
  2. temperatureto reflux for 12 hours
  3. customthe volatiles were removed under vacuum
  4. additionthe pH was adjusted to 7 by addition of solid NaHCO3
  5. extractionThe resulting emulsion was extracted with dichloromethane (4×150 mL)
  6. washThe combined organic solutions were washed with water 1×200 mL),
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-4893bbb2470641aeaf80028a1dcfad75
出典データセット
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06750342B1

反応ノート

読み込み中…

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