Diisopropylcarbodiimide → HCID 54181953、化合物

HRID 613216

反応式

HRID 613216 の反応式
[C:1]([O:5][C:6]([N:8]([CH2:43][C:44]([S:47][C:48]([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([CH3:46])[CH3:45])[CH2:9][CH2:10][N:11]([CH2:19][C:20]([CH3:42])([S:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:21])[CH2:12][CH2:13][CH2:14][CH2:15][C:16](O)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:70]=C=NC(C)C)(C)C.ON1C(=O)CCC1=O.NCCN(CCN)CCN>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH2:43][C:44]([S:47][C:48]([C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)([CH3:45])[CH3:46])[CH2:9][CH2:10][N:11]([CH2:19][C:20]([CH3:42])([S:22][C:23]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH3:21])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH2:70])=[O:17])=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 12734DiisopropylcarbodiimideHCID 77731Tris(2-aminoethyl)amineHCID 80170N-HydroxysuccinimideHCID 53724287HCID 53724287、化合物

生成物 1

HCID 54181953HCID 54181953、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

BAT-BM was prepared as follows. BAT acid (N9 -(t-butoxycarbonyl)-N6,N9 -bis(2-methyl-2-triphenylmethylthiopropyl)-6,9-diazanonanoic acid) (10.03 g, 10.89 mmol) and 75 mL of dry methylene chloride (CH2Cl2) were added to a 250 mL round-bottomed flask equipped with magnetic stir bar and argon balloon. To this solution was added diisopropylcarbodiimide (3.40 mL, 21.7 mmol, 199 mole %), followed by N-hydroxysuccinimide (3.12g, 27.1 mmol, 249 mole %). This solution was observed to become cloudy within 1 h, and was further incubated with stirring for a total of 4 h at room temperature. A solution of tris(2-aminoethyl)amine (30 mL, 200 mmol, 1840 mole %) in 30 mL methylene chloride was then added and stirring continued overnight. The reaction mixture was then concentrated under reduced pressure, and the residue partitioned between ethylacetate (150 mL) and 0.5M potassium carbonate (K2CO3 ; 150 mL). The organic layer was separated, washed with brine and concentrated to give the crude product N-[2-N',N'-bis(2-aminoethyl)aminoethyl)]-N9 -(t-butoxycarbonyl)-N6,N9 -bis(2-methyl-2-triphenylmethylthiopropyl)-6,9-diazanonanamide as a foam/oil.

後処理

  1. customBAT-BM was prepared
  2. customequipped with magnetic stir bar
  3. customwithin 1 h
  4. stirringstirring continued overnight
  5. concentrationThe reaction mixture was then concentrated under reduced pressure
  6. customthe residue partitioned between ethylacetate (150 mL) and 0.5M potassium carbonate (K2CO3 ; 150 mL)
  7. customThe organic layer was separated
  8. washwashed with brine
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-4ab80fdf31b048899b5e73bf88efd563
出典データセット
uspto-grants-1999_12
特許番号
US06007792

関連ノート

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