Lithium Hydroxide → HCID 131729425, 화합물

HRID 425396노트

반응식

HRID 425396 반응식
[OH-].[Li+].[C:3]([NH:6][CH:7]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[N:21][N:22]([CH3:24])[CH:23]=2)=[CH:15][CH:14]=1)[C:8](OC)=[O:9])(=[O:5])[CH3:4].C(=O)(O)[O-].[Na+].[NH2:38][CH2:39][CH:40]([OH:47])[CH2:41][C:42]([CH3:46])([CH3:45])[CH2:43][CH3:44].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>O1CCCC1.O.O.C(Cl)Cl>[C:29]([O:28][C:26](=[O:27])[NH:25][C:20]1[C:19]([C:16]2[CH:17]=[CH:18][C:13]([CH2:12][CH:7]([NH:6][C:3](=[O:5])[CH3:4])[C:8]([NH:38][CH2:39][CH:40]([OH:47])[CH2:41][C:42]([CH3:46])([CH3:45])[CH2:43][CH3:44])=[O:9])=[CH:14][CH:15]=2)=[CH:23][N:22]([CH3:24])[N:21]=1)([CH3:31])([CH3:30])[CH3:32]

참가 물질

10

반응물 6

HCID 3939Lithium HydroxideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 55289824HCID 55289824, 화합물HCID 66705663methyl 2-(acetylamino)-3-(4-{3-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrazol-4-yl}phenyl)propanoate

생성물 1

HCID 131729425HCID 131729425, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

Lithium hydroxide (444 mg, 10.8 mmol) was added to an ambient temperature solution of methyl 2-(acetylamino)-3-(4-{3-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrazo 1-4-yl}phenyl)propanoate (450 mg, 1.08 mmol) in tetrahydrofuran/water (10:1) (11 mL). After stirring at ambient temperature for 1 h, the reaction mixture was diluted with water and extracted with ethyl acetate. The aqueous phase was acidified with 1.5 N hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Sodium bicarbonate (727 mg, 8.66 mmol) was added to an ambient temperature solution of the crude residue, 1-amino-4,4-dimethylhexan-2-ol (314 mg, 2.16 mmol), 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (415 mg, 2.16 mmol) and 1-hydroxybenzotriazole (292 mg, 2.16 mmol) in methylene chloride (20 mL). After stirring at ambient temperature overnight, the reaction was quenched with water and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane afforded tert-butyl[4-(4-{2-(acetylamino)-3-[(2-hydroxy-4,4-dimethylhexyl)amino]-3-oxopropyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate.

후처리

  1. extractionextracted with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo
  5. stirringAfter stirring at ambient temperature overnight
  6. customthe reaction was quenched with water
  7. extractionextracted with methylene chloride and ethyl acetate
  8. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5d6538de3d7a408980d87525ea0b714b
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106070B2

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