Dichloromethane → HCID 54547486, compound

HRID 24670Notes

Reaction equation

HRID 24670 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C@H:9]([C:25]([OH:27])=[O:26])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])=[CH:13][CH:12]=2)=[O:7])=[C:4]([Cl:30])[CH:3]=1.[C:31]([N:38]1[CH:42]=[CH:41]N=C1)(N1C=CN=C1)=[S:32].C(N)[C:44]1[CH:49]=[CH:48]C=[CH:46][CH:45]=1.[CH2:51](Cl)Cl>CN(C=O)C>[CH3:51][O:26][C:25](=[O:27])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[CH:15][CH:16]=1)[NH:8][C:6](=[O:7])[C:5]1[CH:28]=[CH:29][C:2]([NH:1][C:31]([NH:38][CH2:42][C:41]2[CH:48]=[CH:49][CH:44]=[CH:45][CH:46]=2)=[S:32])=[CH:3][C:4]=1[Cl:30]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7504BenzylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 53807261N-(4-amino-2-chlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine

Product 1

HCID 54547486HCID 54547486, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-(4-amino-2-chlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine (57 mg) in DMF (1.5 mL) was added to a solution of 1,1′-thiocarbonyldiimidazole (28 mg) in DMF (1 mL) under N2 at 0° C. over a 2.5 h period. The mixture was then allowed to warm up slowly to room temperature and stirred for an additional 2 h. Benzylamine (21 μL) was then added and the resulting mixture stirred for 2 h at 80° C. The mixture was concentrated, and the residue was taken up with CH2Cl2 and washed with 1N HCl and water. The organic layer was dried (MgSO4), filtered and evaporated. The residue was purified by preparative TLC (silica gel; eluent: CH2Cl2/MeOH/Et3N 100:1:1) to give a solid. The solid was taken up with CH2Cl2 and washed with 1N HCl, dried and evaporated to give N-[4-(3-benzylthioureido)-2-chlorobenzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (42 mg).

Workup

  1. stirringthe resulting mixture stirred for 2 h at 80° C
  2. concentrationThe mixture was concentrated
  3. washwashed with 1N HCl and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by preparative TLC (silica gel; eluent: CH2Cl2/MeOH/Et3N 100:1:1)
  8. customto give a solid
  9. washwashed with 1N HCl
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-94de884ad30348158d008037f9882bd9
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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