Triethylamine → HCID 59257949, compound

HRID 1864627Notes

Reaction equation

HRID 1864627 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:31]([OH:33])=O)[CH2:19][C:20]3[CH:29]=[C:28]([CH3:30])[C:23]4[NH:24][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:34]=[CH:35][CH:36]=[CH:37][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.[N:67]1([CH2:79][C:80]([O:82][CH2:83][CH3:84])=[O:81])[CH2:72][CH2:71][CH:70]([CH:73]2[CH2:78][CH2:77][NH:76][CH2:75][CH2:74]2)[CH2:69][CH2:68]1>C1COCC1.CCOC(C)=O>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C@H:18]([CH2:19][C:20]3[CH:29]=[C:28]([CH3:30])[C:23]4[NH:24][C:25](=[O:27])[O:26][C:22]=4[CH:21]=3)[C:31]([N:76]3[CH2:75][CH2:74][CH:73]([CH:70]4[CH2:69][CH2:68][N:67]([CH2:79][C:80]([O:82][CH2:83][CH3:84])=[O:81])[CH2:72][CH2:71]4)[CH2:78][CH2:77]3)=[O:33])=[O:16])[CH2:13][CH2:14]2)[CH2:7][CH2:6][C:5]2[CH:34]=[CH:35][CH:36]=[CH:37][C:4]=2[NH:3]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22945803Ethyl [4,4′-bipiperidine]-1-acetateHCID 68608307(R)-1-carboxy-2-(4-methyl-2-oxo-2,3-dihydrobenzoxazol-6-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Product 1

HCID 59257949HCID 59257949, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 350 mg (0.69 mmol) (R)-1-carboxy-2-(4-methyl-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, 244 mg (0.76 mmol) TBTU and 138 μL (1.04 mmol) triethylamine in 15 mL THF was stirred for 1 h at RT. Then 175 mg (0.69 mmol) ethyl [4,4′]bipiperidinyl-1-yl-acetate were added. The reaction mixture was stirred for 4 h at RT. The solvent was eliminated i.vac., the residue was taken up in 30 mL EtOAc, the organic phase was washed with 30 mL 5% NaHCO3 solution and dried on Na2SO4. After the desiccant and solvent had been eliminated the residue was purified by chromatography (silica gel, gradient DCM/EtOH 19:1 to DCM/EtOH 9:1). The fractions containing the product were combined and evaporated down i. vac.

Workup

  1. washthe organic phase was washed with 30 mL 5% NaHCO3 solution
  2. customdried on Na2SO4
  3. customwas purified by chromatography (silica gel, gradient DCM/EtOH 19:1 to DCM/EtOH 9:1)
  4. additionThe fractions containing the product
  5. customevaporated down i

Sources & evidence

ORD record
ord-98412e560266404a8221d24e3cb9b4d7
Source dataset
uspto-grants-2009_12
Patent number
US07625886B2

Reaction notes

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