Triethylamine → ethyl 2-{[N-(tert-butoxycarbonyl)glycyl]amino}-3-oxobutanoate

HRID 869723노트

반응식

HRID 869723 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:13][CH:14]([C:20](=[O:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:13][CH:14]([C:20](=[O:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

8

반응물 6

HCID 8471Triethylamine2회HCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13282896Ethyl 2-amino-3-oxobutanoate

생성물 1

HCID 86674522ethyl 2-{[N-(tert-butoxycarbonyl)glycyl]amino}-3-oxobutanoate

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

N-(tert-butoxycarbonyl)glycine (22.4 g, 128 mmol), ethyl 2-amino-3-oxobutanoate (21.1 g, 116 mmol), ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (28.9 g, 151 mmol), 1-hydroxybenzotriazole (23.1 g, 151 mmol), triethylamine (16.2 mL, 116 mmol), in chloroform (350 mL) was stirred for 13 h at room temperature, and then triethylamine (20.0 mL, 143 mmol) was added. After being stirred for 4 h at same temperature, the reaction mixture was poured into saturated aqueous sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted with chloroform. The organic layer was combined, washed with saturated brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The crude was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1) to give ethyl 2-{[N-(tert-butoxycarbonyl)glycyl]amino}-3-oxobutanoate. MS (APCI): m/z 320 (M+NH4), 303 (M+H).

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with chloroform
  3. washwashed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1)

출처 및 근거

ORD 기록
ord-8983b1be36f341beb89be8d9f07c0b02
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969376B2

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