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

HRID 1084526Notes

Reaction equation

HRID 1084526 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 1.0M 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. Chromatography 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.).

Workup

  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. washChromatography 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.

Sources & evidence

ORD record
ord-4719a0441be144ecac4e592f34c9c459
Source dataset
uspto-grants-1991_04
Patent number
US05004741

Reaction notes

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