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 1632173노트

반응식

HRID 1632173 반응식
[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]

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a1b6634c6d87468b8a82f3fb5d400a40
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04474777

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