Methyl iodide → RA Vii

HRID 1632672ノート

反応式

HRID 1632672 の反応式
[CH3:1]OC.[CH3:4][C@@H:5]1[NH:40][C:38](=[O:39])[C@@H:37]2[N:41]([CH3:44])[C:42](=[O:43])[C@@H:21]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[C:34]([CH2:36]2)[CH:33]=[CH:32][C:31]=4[OH:45])=[CH:25][CH:24]=3)[N:20]([CH3:46])[C:18](=[O:19])[C@@H:17]([CH3:47])[NH:16][C:14](=[O:15])[C@H:13]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[N:12]([CH3:57])[C:10](=[O:11])[C@H:9]([CH3:58])[NH:8][C:6]1=[O:7].C[C@@H]1NC(=O)[C@@H]2N(C)C(=O)[C@@H](CC3C=CC(OC4C=C(C2)C=CC=4O)=CC=3)N(C)C(=O)[C@@H](C)NC(=O)[C@H](CC2C=CC(OC)=CC=2)N(C)C(=O)[C@H](C)NC1=O.C[C@@H]1NC(=O)[C@@H]2N(C)C(=O)[C@@H](CC3C=CC(OC4C=C(C2)C=CC=4O)=CC=3)N(C)C(=O)[C@@H](C)NC(=O)[C@H](CC2C=CC(OC)=CC=2)N(C)C(=O)[C@H](C)NC1=O.C[C@@H]1NC(=O)[C@@H]2N(C)C(=O)[C@@H](CC3C=CC(OC4C=C(C2)C=CC=4O)=CC=3)N(C)C(=O)[C@@H](C)NC(=O)[C@H](CC2C=CC(OC)=CC=2)N(C)C(=O)[C@H](C)NC1=O.O.O.O.O.O.CI>COCCOC>[CH3:4][C@H:5]1[NH:40][C:38](=[O:39])[C@H:37]2[N:41]([CH3:44])[C:42](=[O:43])[C@H:21]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[C:34]([CH2:36]2)[CH:33]=[CH:32][C:31]=4[O:45][CH3:1])=[CH:25][CH:24]=3)[N:20]([CH3:46])[C:18](=[O:19])[C@H:17]([CH3:47])[NH:16][C:14](=[O:15])[C@H:13]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[N:12]([CH3:57])[C:10](=[O:11])[C@H:9]([CH3:58])[NH:8][C:6]1=[O:7]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 8254Dimethyl EtherHCID 11979419Bouvardin, 5-(N-methyl-L-tyrosine)-

生成物 1

HCID 3034401RA Vii

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

In 10 ml of anhydrous 1,2-dimethoxy ethane, 100 mg of the methylether derivative of TPC-A was dissolved and 240 mg of potassium fluoride-alumina and excess amount of methyl iodide were added and the mixture was shielded from the light while stirring at room temperature overnight. After completion of the reaction, the solution was filtered, the filtrate was subjected to distillation in vacuo to remove solvent and the residue obtained was purified by P-TLC followed by the recrystallization from methanol to obtain N-methyl derivative of the methylether of TPC-A (98 mg) as colorless crystal having m.p. of 285° to 292° C. (decomp) and [α]D27 of -166° (CHCl3).

後処理

  1. customAfter completion of the reaction
  2. filtrationthe solution was filtered
  3. distillationthe filtrate was subjected to distillation in vacuo
  4. customto remove solvent
  5. customthe residue obtained
  6. customwas purified by P-TLC
  7. customfollowed by the recrystallization from methanol

出典と根拠

ORDレコード
ord-c37596a28787446e96f95a885c9270aa
出典データセット
uspto-grants-1984_10
特許番号
US04476299

反応ノート

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