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 1632173ノート

反応式

HRID 1632173 の反応式
[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]

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a1b6634c6d87468b8a82f3fb5d400a40
出典データセット
uspto-grants-1984_10
特許番号
US04474777

反応ノート

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