Dicyclohexylcarbodiimide → 2H-1,4-Benzodiazepin-2-one, 1,3-dihydro-7-chloro-5-phenyl-3-(phenylmethyl)-, (R)-

HRID 620563ノート

反応式

HRID 620563 の反応式
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.C([NH:24][C@@H:25]([C:33](O)=[O:34])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(OC(C)(C)C)=O.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[Cl:16][C:13]1[CH:14]=[CH:15][C:2]2[NH:1][C:33](=[O:34])[C@@H:25]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:24]=[C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]=2[CH:12]=1

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 128702-Amino-5-chlorobenzophenoneHCID 637610Boc-D-phenylalanine

生成物 1

HCID 27940552H-1,4-Benzodiazepin-2-one, 1,3-dihydro-7-chloro-5-phenyl-3-(phenylmethyl)-, (R)-

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The procedure of Example 1 was carried out using 2-amino-5-chlorobenzophenone (2.32 gm, 0.01 mol), Boc-D-Phenylalanine (2.65 gm, 0.01 mol), and DCC (10 ml of 1.0 M solution in CH2Cl2) in CH2Cl2 (10 ml). After filtration and evaporation, the crude solid was deprotected and cyclized by the procedure of Example 2. After stirring 5 days, the mixture was evaporated in vacuo, treated with H2O (50 ml), and extracted with EtoAc (2×100 ml). The combined organic extracts were washed with brine (50 ml), dried over MgSO4, filtered and evaporated to dryness in vacuo. Chromatogaphy on silica gel eluted with 7.5% (v/v) Et2O in CH2Cl2 gave a white foam which was crystallized from Et2O. The solid was dried in vacuo at 65° C.: (m.p. 154°-7° C.).

後処理

  1. filtrationAfter filtration and evaporation
  2. customthe mixture was evaporated in vacuo
  3. additiontreated with H2O (50 ml)
  4. extractionextracted with EtoAc (2×100 ml)
  5. washThe combined organic extracts were washed with brine (50 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo
  9. washChromatogaphy on silica gel eluted with 7.5% (v/v) Et2O in CH2Cl2
  10. customgave a white foam which
  11. customwas crystallized from Et2O
  12. customThe solid was dried in vacuo at 65° C.

出典と根拠

ORDレコード
ord-d6d59af268fb4425a626e247665e6807
出典データセット
uspto-grants-1989_04
特許番号
US04820834

反応ノート

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