Potassium Carbonate → 2-[3-[(S)-6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]ureido]-2-deoxy-D-glucose

HRID 1632173Notes

Reaction equation

HRID 1632173 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C@H:9]([CH3:14])[N:8]=[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])[C:6]=2[C:22]=1[Br:23].Cl.[OH:25][CH:26]1[O:34][C@H:33]([CH2:35][OH:36])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]1[NH2:28].[C:37](=O)([O-])[O-:38].[K+].[K+]>CC(C)=O.O>[Br:23][C:22]1[C:6]2[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])=[N:8][C@@H:9]([CH3:14])[C:10](=[O:13])[N:11]([CH3:12])[C:5]=2[CH:4]=[CH:3][C:2]=1[NH:1][C:37](=[O:38])[NH:28][C@H:27]([C@H:29]([C@@H:31]([C@@H:33]([CH2:35][OH:36])[OH:34])[OH:32])[OH:30])[CH:26]=[O:25]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochlorideHCID 53936752(S)-7-amino-6-bromo-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 867396682-[3-[(S)-6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]ureido]-2-deoxy-D-glucose

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of (S)-[6-bromo-5-(o-chlorophenyl-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]isocyanate [obtained in accordance with details in Example 1(f) from 10 g (0.0254 mol) of (S)-7-amino-6-bromo-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one] in acetone is treated with a solution of 16 g of D-glucosamine hydrochloride and 7.3 g of potassium carbonate in 100 ml of water, the mixture is stirred at room temperature for 10 minutes and extracted several times with ethyl acetate. The organic phase is dried over sodium sulphate and evaporated, whereupon the residue is recrystallized from tetrahydrofuran/methylene chloride. There is obtained 2-[3-[(S)-6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]ureido]-2-deoxy-D-glucose as a diastereomeric mixture with a melting point of 185° (decomposition); [α]25D =+45° (0.8 percent solution in methanol).

Workup

  1. extractionextracted several times with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. customevaporated, whereupon the residue
  4. customis recrystallized from tetrahydrofuran/methylene chloride

Sources & evidence

ORD record
ord-a1b6634c6d87468b8a82f3fb5d400a40
Source dataset
uspto-grants-1984_10
Patent number
US04474777

Reaction notes

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