4-Methylmorpholine → methyl N-(tert-butoxycarbonyl)-L-leucyl-(5R)-5-((trimethylsilyl)ethynyl)-L-prolinate

HRID 1642654노트

반응식

HRID 1642654 반응식
[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]

참가 물질

7

반응물 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

생성물 1

HCID 66757129methyl N-(tert-butoxycarbonyl)-L-leucyl-(5R)-5-((trimethylsilyl)ethynyl)-L-prolinate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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 M HCl (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)+.

후처리

  1. custompartitioned between ethyl acetate (200 mL) and 1 M HCl (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

출처 및 근거

ORD 기록
ord-0a0f940a9b8241c2ac87367ddb7d0f5d
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119664B2

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