Hydrochloric Acid → HCID 21308799, compound

HRID 442632Notes

Reaction equation

HRID 442632 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:10]([OH:11])[C@@H:9]([OH:12])[C@@H:8]([CH2:13][OH:14])[O:7][C@@H:6]1[NH:15][C:16](=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH2:22])(=[O:3])[CH3:2].Cl>O.[OH-].[Na+].C(Cl)(=O)C=C>[C:1]([NH:4][C@@H:5]1[C@@H:10]([OH:11])[C@@H:9]([OH:12])[C@@H:8]([CH2:13][OH:14])[O:7][C@@H:6]1[NH:15][C:16](=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:6](=[O:7])[CH:5]=[CH2:10])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 21308800HCID 21308800, compound

Product 1

HCID 21308799HCID 21308799, compoundYield 64.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 13140Acryloyl chlorideSolventHCID 14798Sodium HydroxideSolvent

Procedure

The free base 51 (400 mg) was dissolved in a mixture of 1 mL water, 1 mL 2N sodium hydroxide solution and 0.1 mL of acryloyl chloride and the reaction mixture was stirred for 4 hr. The reaction mixture was acidified with 1N HCl and the volatiles were removed from the solution under vacuum. The resulting residue was chromatographed using 5% methanol in dichloromethane to give 52 as a colorless foam (150 mg).

Workup

  1. customthe volatiles were removed from the solution under vacuum
  2. customThe resulting residue was chromatographed

Sources & evidence

ORD record
ord-4a766070bade49e5911e1e24361c6913
Source dataset
uspto-grants-1999_04
Patent number
US05891862

Reaction notes

Loading…