Hydrochloric Acid → Cryptophycin 8

HRID 849817Notes

Reaction equation

HRID 849817 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.O>[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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 6438401Cryptophycin

Product 1

HCID 9918016Cryptophycin 8

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

To a solution of 3.8 mg of Cryptophycin 1 in 1.5 mL of 2:1 1,2-dimethoxyethane/water was added 9 μL 1N HCl. The solution was allowed to stir at room temperature for 4 h, neutralized with potassium carbonate, and evaporated. The residue was partitioned between water and CH2Cl2. The CH2Cl2 -soluble material was purified by reversed-phase HPLC to obtain 3.3 mg of pure Cryptophycin 8.

Workup

  1. customevaporated
  2. customThe residue was partitioned between water and CH2Cl2
  3. customThe CH2Cl2 -soluble material was purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-de81a4854d0a458a96813322d6ef9859
Source dataset
uspto-grants-2000_01
Patent number
US06013626

Reaction notes

Loading…