1,1'-Carbonyldiimidazole → 1,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamate

HRID 573007

반응식

HRID 573007 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:33][NH:34][O:35][CH3:36].C(N(CC)C(C)C)(C)C>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([N:34]([O:35][CH3:36])[CH3:33])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531Diisopropylethylamine

생성물 1

HCID 110559451,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

1000 mg (3.77 mmol) N-(tert-butoxycarbonyl)-L-phenylalanine was placed in 10 mL dichloromethane and mixed with 733 mg (4.52 mmol) 1,1′-carbonyldiimidazole. The batch was stirred for 15 min until the evolution of gas had stopped. Next the mixture was mixed with 441 mg (4.52 mmol) N,O-dimethylhydroxylamine hydrochloride and 657 μL (3.77 mmol) N,N-diisopropylethylamine and stirred for 1 hour at RT. Next the batch was diluted with dichloromethane and washed with distilled water, 0.5N hydrochloric acid and saturated sodium chloride solution in succession. The organic phase was separated and the combined aqueous phases were re-extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated in vacuo, yielding 1090 mg (93% of the theoretical) of the title compound.

후처리

  1. stirringstirred for 1 hour at RT
  2. washwashed with distilled water, 0.5N hydrochloric acid and saturated sodium chloride solution in succession
  3. customThe organic phase was separated
  4. extractionthe combined aqueous phases were re-extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3f716fca4ead4a42841abe5f54d6c286
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029406B2

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