Water → HCID 70505704, compound

HRID 1632175Notes

Reaction equation

HRID 1632175 reaction equation
[Br:1][C:2]1[C:7]2[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])=[N:9][C@@H:10]([CH3:15])[C:11](=[O:14])[N:12]([CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[NH:23][C:24]([NH:26][C:27]([CH2:31][OH:32])([CH2:29][OH:30])[CH3:28])=[O:25].[C:33](OC(=O)C)(=[O:35])[CH3:34].[OH2:40].N1[CH:46]=[CH:45]C=CC=1>>[C:33]([O:32][CH2:31][C:27]([NH:26][C:24]([NH:23][C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH3:13])[C:11](=[O:14])[C@H:10]([CH3:15])[N:9]=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:7]=2[C:2]=1[Br:1])=[O:25])([CH2:29][O:30][C:45](=[O:40])[CH3:46])[CH3:28])(=[O:35])[CH3:34]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 65657Lodazecar

Product 1

HCID 70505704HCID 70505704, compound

Procedure

A solution of 5 g of 1-[(S)-6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-[1,1-bis(hydroxymethyl)ethyl]urea in pyridine is treated with 4 ml of acetic anhydride, the mixture is stirred at room temperature for 1 hour, treated with water and extracted with methylene chloride. The organic phase is dried over sodium sulphate and evaporated, whereupon the residue is chromatographed on silica gel while eluting with chloroform and then recrystallized from petroleum ether. There is obtained (S)-N-[2-(acetyloxy)-1-[(acetyloxy)methyl]-1-methylethyl]-N'-[6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]urea of melting point 105°-107° (decomposition); [α]25D =+33.75° (0.8 percent solution in methylene chloride).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. customevaporated, whereupon the residue
  4. customis chromatographed on silica gel
  5. washwhile eluting with chloroform
  6. customrecrystallized from petroleum ether

Sources & evidence

ORD record
ord-591f0c7d421d4b0ab5b89ded2ffa17dd
Source dataset
uspto-grants-1984_10
Patent number
US04474777

Reaction notes

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