Water → HCID 11113037, compound

HRID 1080379Notes

Reaction equation

HRID 1080379 reaction equation
[OH2:1].[OH-].[Na+].[C:4]1([C:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[NH:14][C:13](=[O:21])[CH:12]([NH:22][C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[N:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:33]1[CH2:38][CH2:37]OCC1>>[C:38]([CH2:37][N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:10]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[N:11][CH:12]([NH:22][C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])[C:13]1=[O:21])([OH:33])=[O:1]

Participants

5

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 2756242Benzyl (2-oxo-5-phenyl-2,3-dihydro-1h-benzo[e][1,4]diazepin-3-yl)carbamate

Product 1

HCID 11113037HCID 11113037, compoundYield 95%

Procedure

Crude product 27 of Example 6 (6 g, 12.73 mmol) was dissolved in dioxane (15 mL) and water (15 mL) and cooled in an ice bath. 2N sodium hydroxide was added to this solution till pH of the solution reached 10. The heterogenous mixture was stirred at room temperature until it became homogenous. The homogenous layer was extracted with ether, and the aqueous layer acidified to pH 2 using 4N HCl. This was extracted with dichloromethane (150×3 mL), and dried over magnesium sulphate to give 5.52 g of 29 (95% yield from compound 26) as a pure white solid.

Workup

  1. extractionThe homogenous layer was extracted with ether
  2. extractionThis was extracted with dichloromethane (150×3 mL)
  3. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-09911197361e4fa7bc0ade328c8b025f
Source dataset
uspto-grants-1996_12
Patent number
US05580979

Reaction notes

Loading…