Hydrochloric Acid → O-(4-fluorophenyl)-L-homoserine ethyl ester hydrochloride

HRID 1836604ノート

反応式

HRID 1836604 の反応式
[C:1]([O:5][C:6](=[O:19])[C@H:7]([CH2:16][CH2:17][OH:18])[NH:8]C(OC(C)(C)C)=O)([CH3:4])(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:39][C:40]1[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=1.N(C(N(C)C)=O)=NC(N(C)C)=O.[ClH:59]>O1CCCC1.C(O)C>[ClH:59].[CH2:1]([O:5][C:6](=[O:19])[C@H:7]([CH2:16][CH2:17][O:18][C:43]1[CH:44]=[CH:45][C:40]([F:39])=[CH:41][CH:42]=1)[NH2:8])[CH3:4]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 11054918(S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

生成物 1

HCID 68613683O-(4-fluorophenyl)-L-homoserine ethyl ester hydrochloride

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of BOC-L-homoserine t-butyl ester (3.2 g, 11.6 mmol) in tetrahydrofuran is added triphenylphosphine (7.59 g, 29 mmol), p-fluorophenol (2.08 g, 18.6 mmol) and 1,1′-azobis(N,N-dimethylformamide) (3.2 g, 18.6 mmol). The mixture is stirred overnight, washed with brine, dried over MgSO4, and the solvent is removed to give an orange oil. The oil is purified by flash chromatography (SiO2, 85% hexane/15% ethyl acetate) to give a clear oil which is dissolved in ethanol (100 mL) and the solution is saturated with HCl gas, then stirred overnight. The mixture is concentrated to give O-(4-fluorophenyl)-L-homoserine ethyl ester hydrochloride as a white solid.

後処理

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. customthe solvent is removed
  4. customto give an orange oil
  5. customThe oil is purified by flash chromatography (SiO2, 85% hexane/15% ethyl acetate)
  6. customto give a clear oil which
  7. stirringstirred overnight
  8. concentrationThe mixture is concentrated

出典と根拠

ORDレコード
ord-3451224190f243ac99dca055d6cf1663
出典データセット
uspto-grants-2004_08
特許番号
US06777443B2

反応ノート

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