1,4,7,10-Tetraazacyclododecane → Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetate

HRID 37049

반응식

HRID 37049 반응식
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[NH:6]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[C:18]([O:22][C:23](=[O:26])[CH2:24]Br)([CH3:21])([CH3:20])[CH3:19]>CN(C)C(=O)C>[C:18]([O:3][C:1](=[O:4])[CH2:2][N:6]1[CH2:17][CH2:16][N:15]([CH2:24][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:26])[CH2:14][CH2:13][N:12]([CH2:24][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:26])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)([CH3:21])([CH3:20])[CH3:19]

참가 물질

5

반응물 3

HCID 649631,4,7,10-TetraazacyclododecaneHCID 79177tert-Butyl bromoacetateHCID 517045Sodium Acetate

생성물 1

HCID 11237632Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetate

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

실험 절차

Sodium acetate (1.23 g, 15 mmol) was added to a stirred suspension of 1,4,7,10 tetraazacyclododecane (0.864 g, 5 mmol) (prepared in accordance with J. Am. Chem. Soc. 96 2268 (1974) and Liebigs Ann. Chem. 1340 (1977)) in N, N-dimethylacetamide (DMA) (15 ml) at ambient temperature. A solution of bromoacetic acid t-butyl ester (2.93 g, 15 mmol) in DMA (8 ml) was added dropwise to the stirred mixture, and the mixture was stirred at ambient temperature for 6 days. The solvent was evaporated and 1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid tri-t-butyl ester was purified by flash chromotography on a silica column with chloroform:methanol 8:2 as eluent. Yield 1.8 g (70%). White solid, m.p. 165°-175° C.

후처리

  1. customThe solvent was evaporated
  2. custom1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid tri-t-butyl ester was purified by flash chromotography on a silica column with chloroform:methanol 8:2 as eluent

출처 및 근거

ORD 기록
ord-42be78bcaad84f48913e55d499736d2f
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05419893

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