Hydrogen Bromide → (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 618593Notes

Reaction equation

HRID 618593 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: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:39]=[CH:40][C:41]([O:45][CH3:46])=[C:42]([Cl:44])[CH:43]=2)[C:5](=[O:6])[NH:4][CH2:3]1.Br.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.C(O)(=O)C>[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:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:27])[CH2:13][CH:12]=[CH:11][C:9](=[O:10])[NH:8][CH:7]([CH2:37][C:38]2[CH:39]=[CH:40][C:41]([O:45][CH3:46])=[C:42]([Cl:44])[CH:43]=2)[C:5](=[O:6])[NH:4][CH2:3]1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 10699481HCID 10699481, compound

Product 1

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-tetroneYield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 7 mg of Cryptophycin 38 in 1 mL of dimethoxyethane was treated with 10 μL of 30% HBr in acetic acid at 50° C. for 18 hours. The mixture was brought to the ambient temperature and stirred with 20 mg of powdered dry potassium carbonate for 3 hours. The solution was filtered, the solvent evaporated and the residue subjected to HPLC on an Econosil silica column (250×10 mm, 5μ, 1:1 ethylacetate/hexane, 3 mL/min) to obtain 3.3 mg of crypptophycin 71 (tR 49.6 min) and 2.8 mg of cryptophycin 72 (tR 46 min).

Workup

  1. customwas brought to the ambient temperature
  2. filtrationThe solution was filtered
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-b0471f3907b9400a8fb9ee423802699d
Source dataset
uspto-grants-1999_09
Patent number
US05952298

Reaction notes

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