HCID 10604239, compound → L 738167

HRID 399439Notes

Reaction equation

HRID 399439 reaction equation
[C:1]1([CH3:45])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C@@H:11]([CH2:15][NH:16][C:17]([C:19]2[CH:44]=[C:22]3[C:23](=[O:43])[N:24]([CH2:28][CH2:29][CH:30]4[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]4)[CH2:25][CH2:26][CH2:27][N:21]3[N:20]=2)=[O:18])[C:12]([OH:14])=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1>C(Cl)Cl>[C:1]1([CH3:45])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C@@H:11]([CH2:15][NH:16][C:17]([C:19]2[CH:44]=[C:22]3[C:23](=[O:43])[N:24]([CH2:28][CH2:29][CH:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)[CH2:25][CH2:26][CH2:27][N:21]3[N:20]=2)=[O:18])[C:12]([OH:14])=[O:13])(=[O:8])=[O:9])=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 10604239HCID 10604239, compound

Product 1

HCID 153986L 738167

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15-1 (7.42 g, 11.48 mmol) was placed in a 1L round bottom flask equipped with a magnetic stir bar. Methylene chloride was added and the reaction mixture was cooled to 0°-5°. Hydrogen chloride was bubbled through the suspension with stirring. After about 2 min. the solid went into solution, and soon afterward a second precipitate formed. After bubbling gas through the suspension for an additional 5 min. the reaction flask was warmed to room temperature. After 30 min. the contents of the reaction flask were concentrated. The resulting white solid was the hydrochloride salt of 15-2 and by HPLC analysis was of >99% purity.

Workup

  1. customequipped with a magnetic stir bar
  2. temperaturethe reaction mixture was cooled to 0°-5°
  3. customHydrogen chloride was bubbled through the suspension
  4. customsoon afterward a second precipitate formed
  5. customAfter bubbling gas through the suspension for an additional 5 min. the reaction flask
  6. concentrationAfter 30 min. the contents of the reaction flask were concentrated

Sources & evidence

ORD record
ord-2c9ef2b2557140458a3b70a13b69bb82
Source dataset
uspto-grants-1998_10
Patent number
US05821241

Reaction notes

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