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 618588Notes

Reaction equation

HRID 618588 reaction equation
[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

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 6438401Cryptophycin

Product 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

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

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)).

Workup

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

Sources & evidence

ORD record
ord-791cb040037a436e857cec2f63f0ebd5
Source dataset
uspto-grants-1999_09
Patent number
US05952298

Reaction notes

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