4-Methylmorpholine → HCID 66757129、化合物

HRID 475336

反応式

HRID 475336 の反応式
[CH3:1][Si:2]([C:5]#[C:6][C@@H:7]1[NH:11][C@H:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:8]1)([CH3:4])[CH3:3].CN(C1C=CC=CN=1)C.CN1CCOCC1.O.[C:33]([O:37][C:38]([NH:40][C@H:41]([C:46](O)=[O:47])[CH2:42][CH:43]([CH3:45])[CH3:44])=[O:39])([CH3:36])([CH3:35])[CH3:34].Cl.CN(C)CCCN=C=NCC>ClCCl>[C:33]([O:37][C:38]([NH:40][C@H:41]([C:46]([N:11]1[C@@H:7]([C:6]#[C:5][Si:2]([CH3:3])([CH3:4])[CH3:1])[CH2:8][CH2:9][C@H:10]1[C:12]([O:14][CH3:15])=[O:13])=[O:47])[CH2:42][CH:43]([CH3:44])[CH3:45])=[O:39])([CH3:35])([CH3:36])[CH3:34]

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12373896N-Boc-L-Leucine HydrateHCID 16090847methyl (5R)-5-((trimethylsilyl)ethynyl)-L-prolinate

生成物 1

HCID 66757129HCID 66757129、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of methyl (5R)-5-((trimethylsilyl)ethynyl)-L-prolinate (1.6 grams, 7.48 mmol), dimethylaminopyridine (913 mg, 7.48 mmol), N-methylmorpholine (1.23 mL, 11.22 mmol), and N-(tert-butoxycabonyl)-L-leucine monohydrate (2.24 g, 8.98 mmol) in dichloromethane (30 mL) at room temperature was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.72 g, 8.98 mmol). The resulting mixture was stirred 16 hours at room temperature, and partitioned between ethyl acetate (200 mL) and 1 MHO (200 mL). The aqueous layer was further extracted with ethyl acetate (200 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated. The residue was chromatographed with a Biotage 40 M cartridge with 40% ethyl acetate/hexane provide the titled compound. MS (DCI/NH3) m/e 439 (M+H)+.

後処理

  1. custompartitioned between ethyl acetate (200 mL) and 1 MHO (200 mL)
  2. extractionThe aqueous layer was further extracted with ethyl acetate (200 mL)
  3. dry with materialThe combined organic layers were dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed with a Biotage 40 M cartridge with 40% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-c31bfe24068f42b18859e38709bc86ef
出典データセット
uspto-grants-2014_01
特許番号
US08637546B2

関連ノート

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