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

HRID 1614518

反応式

HRID 1614518 の反応式
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][CH2:49][OH:50]>CN(C)C=O>[OH:50][CH2:49][CH2:48][CH2:47][N:11]1[CH2:10][CH2:9][N:8]([CH2:7][C:6]([OH:5])=[O:36])[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

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 123133-Chloro-1-propanolHCID 11237632Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetate

生成物 1

HCID 194385111-(3-Hydroxy-propyl)-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1,4,7,10-Tetraazacyclododecane-4,7,10-triacetic acid tri-t-butyl ester (360 mg, 0.70 mmol) (Example 22(a)) was dissolved in dimethylformamide (2.1 ml). Sodium iodide (15 mg, 1 mmol), triethylamine (142 mg, 1.4 mmol) and 3-chloro-1 propanol (132 mg, 1.4 mmol) were added to the stirred mixture at ambient temperature. The mixture was stirred for 3 hours at ambient temperature, the temperature was then raised to 100° C. and kept there for 2 hours. The solvent was evaporated and the residue was dissolved in dichloromethane (3 ml) and washed with water (1 ml). Trifluoroacetic acid (2 ml) was added to the dichloromethane solution and the mixture was stirred at ambient temperature for 1 hour. The solvents were evaporated and the residue dissolved in water (6 ml). The aqueous solution was washed with ether (6×3 ml). The aqueous solution was acidified, the water was evaporated, and the title compound was isolated as a hygroscopic white powder. Yield 192 mg (68%), FAB MS: 405(M+1). The structure was confirmed by 1HNMR and 13CNMR

後処理

  1. temperaturethe temperature was then raised to 100° C.
  2. waitkept there for 2 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane (3 ml)
  5. washwashed with water (1 ml)
  6. additionTrifluoroacetic acid (2 ml) was added to the dichloromethane solution
  7. stirringthe mixture was stirred at ambient temperature for 1 hour
  8. customThe solvents were evaporated
  9. dissolutionthe residue dissolved in water (6 ml)
  10. washThe aqueous solution was washed with ether (6×3 ml)
  11. customthe water was evaporated

出典と根拠

ORDレコード
ord-646e2e55d02340b1bbb1f7fe1644cfde
出典データセット
uspto-grants-1993_03
特許番号
US05198208

関連ノート

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