4-Methylmorpholine → Z-Gly-Leu-PheCH2F

HRID 2373071

反応式

HRID 2373071 の反応式
[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:2][C:3]([NH:5][C@H:6]([C:11]([OH:13])=O)[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4].N(C(OCC1C=CC=CC=1)=O)CC(O)=O.[OH-].[Na+].CN1CCOCC1.[NH2:48][C@H:49]([C:57]([CH2:59][F:60])=[O:58])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.Cl>C1COCC1.CN(C=O)C>[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:2][C:3]([NH:5][C@H:6]([C:11]([NH:48][C@H:49]([C:57]([CH2:59][F:60])=[O:58])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:13])[CH2:7][CH:8]([CH3:9])[CH3:10])=[O:4]

参加物

8

反応物 5

HCID 79724-Methylmorpholine2 回HCID 14349BenzyloxycarbonylglycineHCID 14798Sodium HydroxideHCID 96816Z-Gly-Leu-OH2 回HCID 131717227PheCH2F hydrochloride

生成物 1

HCID 131717229Z-Gly-Leu-PheCH2F収率 54%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Z-Gly-LeuOH was made by mixed anhydride coupling of Z-GlyOH and LeuOBzl tosylate, followed by NaOH hydrolysis of the benzyl ester. To a solution of Z-Gly-LeuOH (0.223 g, 0.69 mmol) in THF (4 mL) at -20° C. was added NMM (76 uL, 0.69 mmol), followed by IBCF (90 uL, 0.69 mmol). After 10 minutes, a precooled solution of PheCH2F hydrochloride (0.15 g, 0.69 mmol) in DMF (1 mL) was added, followed by a second equivalent (76 uL, 0.69 mmol) of NMM. After 30 minutes of stirring, the mixture was quenched with 1M HCl (5 mL), extracted with ethyl acetate (20 mL), washed with saturated aqueous NaHCO3 (6 mL), brine (5 mL), dried over MgSO4, filtered, and evaporated to dryness. The residue was crystallized from ether/hexane to give 0.18 g (54%) of Z-Gly-Leu-PheCH2F.

後処理

  1. customthe mixture was quenched with 1M HCl (5 mL)
  2. extractionextracted with ethyl acetate (20 mL)
  3. washwashed with saturated aqueous NaHCO3 (6 mL), brine (5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was crystallized from ether/hexane

出典と根拠

ORDレコード
ord-1a2cdad7a44c445db5cfed2e12ca1dee
出典データセット
uspto-grants-1992_03
特許番号
US05101068

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