Hydrochloric Acid → Ethyl acetate methanol ammonium hydroxide

HRID 1859203Notes

Reaction equation

HRID 1859203 reaction equation
[C:1]([O:5]C([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([C:25]3[C:26](=[O:41])[NH:27][C:28](=[O:40])[C:29]=3[C:30]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32]([CH3:39])[CH:31]=3)=[CH:17]2)[CH:13]=[CH:14][CH:15]=1)=O)(C)(C)C.Cl.[OH-:43].[NH4+].[C:45]([O:48][CH2:49][CH3:50])(=[O:47])[CH3:46]>>[C:45]([O:48][CH2:49][CH3:50])(=[O:47])[CH3:46].[CH3:1][OH:5].[OH-:43].[NH4+:8].[NH2:8][CH2:9][C:10]1[CH:11]=[C:12]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([C:25]3[C:26](=[O:41])[NH:27][C:28](=[O:40])[C:29]=3[C:30]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32]([CH3:39])[CH:31]=3)=[CH:17]2)[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 22123273HCID 22123273, compound

Product 2

HCID 21901312Ethyl acetate methanol ammonium hydroxideHCID 22123276HCID 22123276, compound

Procedure

The product from step b) (66.0 mg, 0.12 mmol), tetrhydrofuran (5 mL) and 5 mL of 5 M HCl (aq) were heated at 50° C. for 45 min. The mixture was poured into ethyl acetate and dilute ammonium hydroxide. The organic phase was washed 3 times with dilute ammonium hydroxide and once with water, and then evaporated. Chromatography (ethyl acetate/methanol/ammonium hydroxide: 95/5/1) gave 54 mg of the title product.

Workup

  1. washThe organic phase was washed 3 times with dilute ammonium hydroxide
  2. customonce with water, and then evaporated

Sources & evidence

ORD record
ord-d1c6ded105fb429c85831336dba5872a
Source dataset
uspto-grants-2000_11
Patent number
US06153641

Reaction notes

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