Hydrochloric Acid → Z-FF-Fmk

HRID 248589

反応式

HRID 248589 の反応式
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN1CCOCC1.[NH2:30][C@H:31]([C:39]([CH2:41][F:42])=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl.Cl>C1COCC1.CN(C=O)C>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:30][C@H:31]([C:39]([CH2:41][F:42])=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2 回HCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 131717227PheCH2F hydrochloride

生成物 1

HCID 11705307Z-FF-Fmk

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of Z-PheOH (0.207 g, 0.69 mmol) in THF (4 mL), cooled to -20° C., were added NMM (76 uL, 0.69 mmol) and IBCF (90 uL, 0.69 mmol). After 10 minutes, a chilled (-10° C.) solution of PheCH2F hydrochloride (0.15 g, 0.69 mmol) in DMF (1 mL) was added, followed by NMM (76 uL, 0.69 mmol). The mixture was stirred for 30 minutes. 1M HCl (5 mL) was added. The solution was extracted with ethyl acetate (30 mL), washed with saturated aqueous NaHCO3 (6 mL), brine (4 mL), dried over MgSO4, filtered, and evaporated to dryness. The residue was crystallized from ethyl acetate/hexane, yielding 0.22 (53%) of Z-Phe-PheCH2F.

後処理

  1. additionwas added
  2. extractionThe solution was extracted with ethyl acetate (30 mL)
  3. washwashed with saturated aqueous NaHCO3 (6 mL), brine (4 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was crystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-b056866b65314ff4a2dd2e3080fdd500
出典データセット
uspto-grants-1993_05
特許番号
US05210272

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