Hydrochloric Acid → HCID 67332127、化合物

HRID 1988077ノート

反応式

HRID 1988077 の反応式
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH:6]([NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:12])[C:7](O)=[O:8].CCN(CC)CC.ClC(OCC)=O.[BH4-].[Na+].Cl>C1COCC1.CO>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH:6]([NH:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:17][CH:18]=1)=[O:12])[CH2:7][OH:8]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 45496562HCID 45496562、化合物

生成物 1

HCID 67332127HCID 67332127、化合物収率 31%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

2-[(Biphenyl-4-carbonyl)-amino]-pentanedioic acid 5-methyl ester (1.128 g, 3.30 mmol, 1.0 equiv.) was dissolved in THF (35 mL). The mixture was cooled to −20° C., followed by the addition of Et3N (343 mg, 3.3 mmol, 1.0 equiv.) and ethyl chloroformate (358 mg, 3.3 mmol, 1.0 equiv.). After stirring for 20 minutes, NaBH4 (375 mg, 9.9 mmol, 3 equiv.) was added and the temperature was raised to −10° C. After stirring for 5 min, MeOH (30 mL) was introduced and the mixture was further stirred for 20 min at this temperature and then at 0° C. for 20 min. 1N HCl was then added slowly to quench the reaction. Solvent was evaporated and the residue partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over MgSO4, and removed solvent by rotavap. The crude mixture was then purified by column chromatography (silica gel, 3% MeOH/CH2Cl2) to afford 333 mg of 4-[(Biphenyl-4-carbonyl)-amino]-5-hydroxy-pentanoic acid methyl ester in 31% yield. MS (ESI) m/z 328.

後処理

  1. temperaturethe temperature was raised to −10° C
  2. stirringAfter stirring for 5 min
  3. stirringthe mixture was further stirred for 20 min at this temperature
  4. waitat 0° C. for 20 min
  5. customto quench
  6. customthe reaction
  7. customSolvent was evaporated
  8. customthe residue partitioned between EtOAc and H2O
  9. washThe organic layer was washed with brine
  10. dry with materialdried over MgSO4
  11. customremoved solvent by rotavap
  12. customThe crude mixture was then purified by column chromatography (silica gel, 3% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-2e1fc1f0002947ecbaaf7cae425c9308
出典データセット
uspto-grants-2009_06
特許番号
US07553873B2

反応ノート

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