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 618592Notes

Reaction equation

HRID 618592 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.Cl.C(=O)([O-])[O-].[K+].[K+]>CC#N.O>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 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 18.3%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A solution of 6.0 mg of Cryptophycin 38 in 0.5 mL of dimethoxythane was treated with 2 μL concentrated HCl at room temperature. After 12 hours the excess acid was neutralized by stirring with 20 mg of solid potassium carbonate. The reaction mixture was filtered and the solvent evaporated to obtain a residue which was subjected to reversed-phase HPLC (C18, 10 μm, 22×250 mm column, 3:1 CH3CN/H2O, 3 mL/min flow rate) to give 4.3 mg of Cryptophycin 69 (tR 25.6 min) and 1.1 mg of Cryptophycin 70 (tR 24 min).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent evaporated
  3. customto obtain a residue which

Sources & evidence

ORD record
ord-39ddd8da25db4b7abdaf24279ae02195
Source dataset
uspto-grants-1999_09
Patent number
US05952298

Reaction notes

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