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

HRID 869723ノート

反応式

HRID 869723 の反応式
[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]

参加物

8

反応物 6

HCID 8471Triethylamine2 回HCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13282896Ethyl 2-amino-3-oxobutanoate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8983b1be36f341beb89be8d9f07c0b02
出典データセット
uspto-grants-2015_03
特許番号
US08969376B2

反応ノート

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