Dicyclohexylcarbodiimide → 1,3-Dihydro-5-(2-fluorophenyl)-3(RS)-(2-thienyl)methyl-2H-1,4-benzodiazepin-2-one

HRID 1084527

反応式

HRID 1084527 の反応式
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])=O.C([NH:24][CH:25]([C:32](O)=[O:33])[CH2:26][C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)(OC(C)(C)C)=O.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[F:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]1[C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[NH:1][C:32](=[O:33])[CH:25]([CH2:26][C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)[N:24]=1

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 741012-Amino-2'-fluorobenzophenoneHCID 5035100N-Boc-beta-(2-thienyl)-DL-alanine

生成物 1

HCID 156147381,3-Dihydro-5-(2-fluorophenyl)-3(RS)-(2-thienyl)methyl-2H-1,4-benzodiazepin-2-one

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-2'-fluorobenzophenone (1.26 gm, 5.86 mmol), N-Boc-β-(2-thienyl)-DL-alanine (1.75 gm, 6.45 mmol), and DCC (6.45 ml of 1.0M solution in CH2Cl2) in CH2Cl2 (25 ml). Filtration, concentration in vacuo and flash chromatography (silica gel, 1% (v/v) Et2O in CH2Cl2) gave a white foam which was deprotected and cyclized by the procedure of Example 2. After stirring 3 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. The resulting foam was crystallized from Et2O to give the title compound as a white solid. The solid was dried in vacuo at 65° C.: (m.p. 189°-91° C.).

後処理

  1. filtrationFiltration, concentration in vacuo and flash chromatography (silica gel, 1% (v/v) Et2O in CH2Cl2)
  2. customgave a white foam which
  3. customthe mixture was evaporated in vacuo
  4. additiontreated with H2O (50 ml)
  5. extractionextracted with EtOAc (2×100 ml)
  6. washThe combined organic extracts were washed with brine (50 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness in vacuo
  10. customThe resulting foam was crystallized from Et2O

出典と根拠

ORDレコード
ord-be44ebf39bb64895b9c5643b3f3e7122
出典データセット
uspto-grants-1991_04
特許番号
US05004741

関連ノート

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