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 1632174노트

반응식

HRID 1632174 반응식
[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]

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 180Acetone용매2회HCID 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 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).

후처리

  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

출처 및 근거

ORD 기록
ord-4866b5f706aa405695d8bd3c8f00db3c
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04474777

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