3-Amino-1,2-propanediol → 1-[(S)-6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]urea

HRID 1632174ノート

反応式

HRID 1632174 の反応式
[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[N:23]=[C:24]=[O:25].N[C:27]1[CH:28]=CC2N(C)C(=O)[C@H](C)N=C(C3C=CC=CC=3Cl)C=2[C:47]=1Br.[NH2:49][CH2:50][CH:51]([OH:54])[CH2:52][OH:53]>CC(C)=O.O>[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:49][CH2:50][CH:51]1[CH2:52][O:53][C:27]([CH3:28])([CH3:47])[O:54]1)=[O:25]

参加物

6

反応物 3

HCID 735613-Amino-1,2-propanediolHCID 53715566(S)-[6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]isocyanateHCID 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 543347131-[(S)-6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]urea

試薬・触媒・溶媒 2

HCID 180Acetone溶媒2 回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 4 g (0.01 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 3.8 g (0.04 mol) of 3-amino-1,2-propanediol in 10 ml of water and 50 ml of acetone, the mixture is stirred at room temperature for 12 hours and extracted with methylene chloride. The organic extract is dried over sodium sulphate and evaporated, whereupon the residue is chromatographed on silica gel while eluting with chloroform. There is obtained 1-[(S)-6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]urea of melting point 135° (decomposition); [α]25D =+7.6° (0.8 percent solution in methanol).

後処理

  1. extractionextracted with methylene chloride
  2. extractionThe organic extract
  3. dry with materialis dried over sodium sulphate
  4. customevaporated, whereupon the residue
  5. customis chromatographed on silica gel
  6. washwhile eluting with chloroform

出典と根拠

ORDレコード
ord-4866b5f706aa405695d8bd3c8f00db3c
出典データセット
uspto-grants-1984_10
特許番号
US04474777

反応ノート

読み込み中…