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 618588노트

반응식

HRID 618588 반응식
[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

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 6438401Cryptophycin

생성물 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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

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)).

후처리

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

출처 및 근거

ORD 기록
ord-791cb040037a436e857cec2f63f0ebd5
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952298

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