Hydrochloric Acid → (13E)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[1-(3-phenyloxiran-2-yl)ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone

HRID 618588ノート

反応式

HRID 618588 の反応式
[CH3:1][C@H:2]1[C:20](=[O:21])[O:19][C@@H:18]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:16](=[O:17])[O:15][C@H:14]([C@@H:26]([C@H:28]2[O:30][C@@H:29]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:27])[CH2:13][CH:12]=[CH:11][C:9](=[O:10])[NH:8][C@H:7]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([Cl:46])[CH:39]=2)[C:5](=[O:6])[NH:4][CH2:3]1.[ClH:47].C(=O)([O-])[O-].[K+].[K+]>COCCOC>[CH3:1][C@H:2]1[C:20](=[O:21])[O:19][C@@H:18]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:16](=[O:17])[O:15][C@H:14]([C@@H:26]([C@@H:28]([OH:30])[C@@H:29]([Cl:47])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH3:27])[CH2:13][CH:12]=[CH:11][C:9](=[O:10])[NH:8][C@H:7]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([Cl:46])[CH:39]=2)[C:5](=[O:6])[NH:4][CH2:3]1.[CH3:1][CH:2]1[C:20](=[O:21])[O:19][CH:18]([CH2:22][CH:23]([CH3:24])[CH3:25])[C:16](=[O:17])[O:15][CH:14]([CH:26]([CH:28]2[O:30][CH:29]2[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH3:27])[CH2:13][CH:12]=[CH:11][C:9](=[O:10])[NH:8][CH:7]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([Cl:46])[CH:39]=2)[C:5](=[O:6])[NH:4][CH2:3]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 6438401Cryptophycin

生成物 2

HCID 5468287(13E)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[1-(3-phenyloxiran-2-yl)ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetroneHCID 9918016Cryptophycin 8

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a solution of Cryptophycin 1 (500 mg) in 3 mL of 1,2-dimethoxyethane was added 60 μL of concentrated HCl. The mixture was stirred at room temperature for 18 h, potassium carbonate (50 mg) was added, and the mixture was stirred for an additional 2 h, then filtered and evaporated. The residue was subjected to reversed-phase HPLC (Alltech Econosil C18, 250 mm×22 mm column, flow rate 5 mL/min, 20 mg/injection, UV detection at 254 nm) using 3:1 MeCN/H2O to give 433 mg of Cryptophycin 8 (tR 25 min) and 16 mg of Cryptophycin 27 (tR 21 min)).

後処理

  1. stirringthe mixture was stirred for an additional 2 h
  2. filtrationfiltered
  3. customevaporated

出典と根拠

ORDレコード
ord-791cb040037a436e857cec2f63f0ebd5
出典データセット
uspto-grants-1999_09
特許番号
US05952298

反応ノート

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