Trifluoroacetic acid → HCID 11542145, compound

HRID 642831Notes

Reaction equation

HRID 642831 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:32](O)=[O:33])[CH2:19][C:20]3[CH:30]=[C:29]([CH3:31])[C:23]4[N:24]([CH3:28])[C:25](=[O:27])[O:26][C:22]=4[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:35]=[CH:36][CH:37]=[CH:38][C:4]=2[NH:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[CH3:68][C:69]1([NH:81]C(=O)OC(C)(C)C)[CH2:74][CH2:73][N:72]([CH:75]2[CH2:80][CH2:79][NH:78][CH2:77][CH2:76]2)[CH2:71][CH2:70]1.C(O)(C(F)(F)F)=O>CN(C=O)C.C(Cl)Cl>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:19][C:20]3[CH:30]=[C:29]([CH3:31])[C:23]4[N:24]([CH3:28])[C:25](=[O:27])[O:26][C:22]=4[CH:21]=3)[C:32]([N:78]3[CH2:79][CH2:80][CH:75]([N:72]4[CH2:73][CH2:74][C:69]([NH2:81])([CH3:68])[CH2:70][CH2:71]4)[CH2:76][CH2:77]3)=[O:33])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:35]=[CH:36][CH:37]=[CH:38][C:4]=2[NH:3]1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68610200HCID 68610200, compoundHCID 91199855HCID 91199855, compound

Product 1

HCID 11542145HCID 11542145, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 80 mg (0.15 mmol) (R)-1-carboxy-2-(3,4-dimethyl-2-oxo-2,3-dihydrobenz-oxazol-6-yl)-ethyl 4-(2-oxo-1,2,4,5,-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 58 mg (0.18 mmol) TBTU, 140 μL (1.00 mmol) triethylamine and 59 mg (0.16 mmol) tert.-butyl (4-methyl-[1,4′]bipiperidinyl-4-yl)-carbamate in 1.8 mL DMF were stirred overnight at RT. The reaction mixture was purified by HPLC, the fractions containing the product were combined and lyophilised. The residue obtained was dissolved in 4 mL DCM, combined with 0.5 mL TFA and the reaction solution was stirred for 5 h at RT. The DCM was left to evaporate off overnight, the residue was combined with 2 mL 15% K2CO3 solution and extracted twice with 2 mL DCM. After the solvent had been eliminated the residue was taken up in 1 mL DMF and purified by HPLC. The fractions containing the product were combined and lyophilised.

Workup

  1. customThe reaction mixture was purified by HPLC
  2. additionthe fractions containing the product
  3. customThe residue obtained
  4. customto evaporate off overnight
  5. extractionextracted twice with 2 mL DCM
  6. custompurified by HPLC
  7. additionThe fractions containing the product

Sources & evidence

ORD record
ord-8c84d6185b9f42d9a440e204f3807606
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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