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

HRID 1084527

반응식

HRID 1084527 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-be44ebf39bb64895b9c5643b3f3e7122
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05004741

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