Hydrochloric Acid → (2R)-2-{[10-(4-Cyclohex-1-en-1-yl-3-methyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carbonyl]-amino}-3-hydroxy-propionic acid

HRID 489585Notes

Reaction equation

HRID 489585 reaction equation
C[O:2][C:3](=[O:39])[C@H:4]([NH:7][C:8]([C:10]1[N:19]2[C:13]([CH2:14][N:15]([C:24](=[O:38])[C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]=4)=[C:27]([CH3:37])[CH:26]=3)[C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[CH2:18]2)=[CH:12][CH:11]=1)=[O:9])[CH2:5][OH:6].[OH-].[Na+].Cl>CC(C)=O>[C:31]1([C:28]2[CH:29]=[CH:30][C:25]([C:24]([N:15]3[C:16]4[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=4[CH2:18][N:19]4[C:10]([C:8]([NH:7][C@H:4]([CH2:5][OH:6])[C:3]([OH:39])=[O:2])=[O:9])=[CH:11][CH:12]=[C:13]4[CH2:14]3)=[O:38])=[CH:26][C:27]=2[CH3:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10208562HCID 10208562, compound

Product 1

HCID 69793572(2R)-2-{[10-(4-Cyclohex-1-en-1-yl-3-methyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carbonyl]-amino}-3-hydroxy-propionic acidYield 98.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(2R)-2-{[10-(4-Cyclohex-1-en-1-yl-3-methyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carbonyl]-amino}-3-hydroxy-propionic acid methyl ester of Example 13 (0.260 g, 0.493 mmol), was dissolved in acetone (3.3 mL), followed by the addition of 2.5 N sodium hydroxide (0.590 mL, 1.48 mmol). The reaction was stirred at room temperature overnight, acidified with 1 N hydrochloric acid and extracted with diethyl ether. The combined ether phases were extracted with 1 N sodium hydroxide and the basic extracts acidified with 2 N hydrochloric acid. The acidified extracts were extracted with diethyl ether and the combined ether extracts dried over anhydrous magnesium sulfate, filtered and concentrated to afford 0.250 g of the title compound as a white powder.

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe combined ether phases were extracted with 1 N sodium hydroxide
  3. extractionThe acidified extracts were extracted with diethyl ether
  4. dry with materialthe combined ether extracts dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-021e26e15ef748eba6fa52492b2d5abf
Source dataset
uspto-grants-2005_12
Patent number
US06977254B2

Reaction notes

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