Sodium Iodide → 1-(5-Hydroxy-3-oxapentyl)-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid

HRID 37050

반응식

HRID 37050 반응식
C([O:5][C:6](=[O:36])[CH2:7][N:8]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[CH2:16][CH2:15][N:14]([CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)(C)(C)C.[I-].[Na+].C(N(CC)CC)C.Cl[CH2:47][CH2:48][O:49][CH2:50][CH2:51][OH:52]>CN(C)C=O>[OH:52][CH2:51][CH2:50][O:49][CH2:48][CH2:47][N:11]1[CH2:10][CH2:9][N:8]([CH2:7][C:6]([OH:36])=[O:5])[CH2:19][CH2:18][N:17]([CH2:20][C:21]([OH:23])=[O:22])[CH2:16][CH2:15][N:14]([CH2:28][C:29]([OH:31])=[O:30])[CH2:13][CH2:12]1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 123612-(Chloroethoxy)ethanolHCID 11237632Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetate

생성물 1

HCID 194385451-(5-Hydroxy-3-oxapentyl)-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1,4,7,10-Tetraazacyclododecane-4,7,10-triacetic acid tri-t-butyl-ester (515 mg, 1 mmol) was dissolved in dimethylformamide (3 ml). Sodium iodide (15 mg, 0.1 mmol), triethylamine (233 mg, 2.5 mmol) and 2(2-chloroethoxy) ethanol (313 mg, 3.5 mmol) were added to the stirred mixture at ambient temperature. The mixture was stirred for 18 hours at ambient temperature. The temperature was then raised to 100° C. and kept there for 1 hour. The solvent was then evaporated and the residue dissolved in a mixture of dichloromethane (4.5 ml) and trifluoroacetic acid (4.5 ml). The mixture was stirred for 2 hours at ambient temperature and the solvent was then evaporated. The residue was dissolved in water (8 ml), and this aqueous solution was washed with ether (6×4 ml). The aqueous solution was acidified and the title compound was isolated as a hygroscopic white powder after evaporation of the water. Yield 325 mg (75%), FAB MS: 435(M+1 ). The structure was confirmed by 1HNMR and 13C NMR.

후처리

  1. temperatureThe temperature was then raised to 100° C.
  2. waitkept there for 1 hour
  3. customThe solvent was then evaporated
  4. dissolutionthe residue dissolved in a mixture of dichloromethane (4.5 ml) and trifluoroacetic acid (4.5 ml)
  5. stirringThe mixture was stirred for 2 hours at ambient temperature
  6. customthe solvent was then evaporated
  7. dissolutionThe residue was dissolved in water (8 ml)
  8. washthis aqueous solution was washed with ether (6×4 ml)

출처 및 근거

ORD 기록
ord-a09a9c54bb3348709006ef40b418f2b8
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05419893

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