1-Hydroxybenzotriazole → HCID 69068234, compound

HRID 643145Notes

Reaction equation

HRID 643145 reaction equation
[CH2:1]([O:8][C:9]1[C:24]([CH3:25])=[CH:23][C:12]([CH2:13][C@@H:14]([CH2:19][C:20]([O-:22])=O)[C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=1[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C.[NH:68]1[CH2:73][CH2:72][CH:71]([N:74]2[CH2:80][CH2:79][C:78]3[CH:81]=[CH:82][CH:83]=[CH:84][C:77]=3[NH:76][C:75]2=[O:85])[CH2:70][CH2:69]1>C1COCC1.CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9]1[C:10]([CH3:26])=[CH:11][C:12]([CH2:13][C@@H:14]([CH2:19][C:20](=[O:22])[N:68]2[CH2:69][CH2:70][CH:71]([N:74]3[CH2:80][CH2:79][C:78]4[CH:81]=[CH:82][CH:83]=[CH:84][C:77]=4[NH:76][C:75]3=[O:85])[CH2:72][CH2:73]2)[C:15]([O:17][CH3:18])=[O:16])=[CH:23][C:24]=1[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 86632853HCID 86632853, compound

Product 1

HCID 69068234HCID 69068234, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.69 g (4.74 mmol) 1-methyl (S)-2-(4-benzyloxy-3,5-dimethyl-benzyl)-succinate, 1.55 g (4.83 mmol) TBTU, 0.69 g (5.10 mmol) HOBt and 1.34 mL (7.71 mmol) ethyldiisopropylamine in 40 mL THF and 5 mL DMF was stirred for 16 h at RT. Then 1.16 g (4.74 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one was added to the reaction mixture, which was then stirred for a further 2.5 h at RT. The reaction solution was combined with 40 mL EtOAc, the organic phase was washed twice with 30 mL semisaturated NaHCO3 and once with 40 mL saturated NaCl solution washed and dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was purified by chromatography (silica gel, EtOAc/Cyc 3:1).

Workup

  1. stirringwas then stirred for a further 2.5 h at RT
  2. washthe organic phase was washed twice with 30 mL
  3. washonce with 40 mL saturated NaCl solution washed
  4. dry with materialdried over Na2SO4
  5. customwas purified by chromatography (silica gel, EtOAc/Cyc 3:1)

Sources & evidence

ORD record
ord-8b8bf54feb6a42abb7a5f921c94b8e9f
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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