Triethylamine → HCID 22883383, compound

HRID 1924Notes

Reaction equation

HRID 1924 reaction equation
[CH:1]1[C:13]2C(COC(N[C@H](CCC3C=CC=CC=3)C(O)=O)=O)C3[C:6](=[CH:7]C=CC=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:31](Cl)(=[O:35])[C:32](Cl)=O.[CH3:37][NH:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:51]#[N:52])=[CH:41][CH:40]=1.C([N:55](CC)CC)C>CN(C=O)C.C(Cl)Cl>[NH2:55][C@H:32]([CH2:7][CH2:6][C:5]1[CH:13]=[CH:1][CH:2]=[CH:3][CH:4]=1)[C:31]([N:38]([CH3:37])[C:39]1[CH:40]=[CH:41][C:42]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:51]#[N:52])=[CH:43][CH:44]=1)=[O:35]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 7129818Fmoc-D-Homophe-OHHCID 19692827HCID 19692827, compound

Product 1

HCID 22883383HCID 22883383, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(R)-α-[N-(9-Fluorenylmethoxycarbonyl)amino]-benzenebutanoic acid (500 mg; 1.25 mmol), was converted into its corresponding acid chloride according to the procedure descibed in Example 33, Step F using 1 drop of DMF, oxalyl chloride (136 μl) in methylene chloride (2.5 ml). A yellow solid which was the acid chloride (525 mg) was obtained and used without further purification. A portion of the acid chloride (222.8 mg; 0.528 mmol) was added to 4-[N-methylamino]-2'-cyano-1,1'-biphenyl (110 mg; 0.528 mmol) were dissolved in methylene chloride (1 ml) and stirred together for 2 h at room temperature. Triethylamine (73.6 μl; 0.528 mmol) was added and the reaction mixture stirred for a further 6 h. The reaction was quenched with 4-(aminomethyl)-piperidine (0.5 ml) and stirred for 15 minutes and then partitioned between water and methylene chloride. The organic phase was separated, dried over powdered potassium carbonate. The volatiles were removed under reduced pressure and the residues chromatographed on silica gel using ethyl acetate and then ethyl acetate and methanol 9:1 v/v. The yield of the desired product was 60.2 mg (30.8%). FAB-MS:- calculated for C24H23N30 369.2 found 370.0 (M+1).

Workup

  1. customwas obtained
  2. customused without further purification
  3. stirringthe reaction mixture stirred for a further 6 h
  4. customThe reaction was quenched with 4-(aminomethyl)-piperidine (0.5 ml)
  5. stirringstirred for 15 minutes
  6. custompartitioned between water and methylene chloride
  7. customThe organic phase was separated
  8. customdried
  9. customThe volatiles were removed under reduced pressure
  10. customthe residues chromatographed on silica gel

Sources & evidence

ORD record
ord-f701c8034cd64527bb66e1cb9184c5a6
Source dataset
uspto-grants-1998_03
Patent number
US05726319

Reaction notes

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