1-Hydroxybenzotriazole → HCID 86759011, compound

HRID 1369275Notes

Reaction equation

HRID 1369275 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:23]([O:25][P:26]([C:31]1[CH:32]=[C:33]([CH2:49][CH2:50][C:51]([OH:53])=O)[CH:34]=[CH:35][C:36]=1[O:37][CH2:38][P:39]([O:45][CH:46]([CH3:48])[CH3:47])([O:41][CH:42]([CH3:44])[CH3:43])=[O:40])([O:28][CH2:29][CH3:30])=[O:27])[CH3:24].[C:54]([C:57]1[CH:58]=[C:59]([CH:71]([NH2:73])[CH3:72])[CH:60]=[CH:61][C:62]=1[O:63][CH2:64][CH:65]1[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]1)(=[O:56])[NH2:55]>C(Cl)Cl.CN(C=O)C>[CH2:29]([O:28][P:26]([C:31]1[CH:32]=[C:33]([CH2:49][CH2:50][C:51](=[O:53])[NH:73][CH:71]([C:59]2[CH:60]=[CH:61][C:62]([O:63][CH2:64][CH:65]3[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70]3)=[C:57]([C:54](=[O:56])[NH2:55])[CH:58]=2)[CH3:72])[CH:34]=[CH:35][C:36]=1[O:37][CH2:38][P:39]([O:45][CH:46]([CH3:47])[CH3:48])([O:41][CH:42]([CH3:44])[CH3:43])=[O:40])(=[O:27])[O:25][CH2:23][CH3:24])[CH3:30]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11437350HCID 11437350, compoundHCID 54234541HCID 54234541, compound

Product 1

HCID 86759011HCID 86759011, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

HOBt (94 mg, 0.69 mmol) and EDC.HCl (140 mg, 0.73 mmol) were dissolved in 2.5 mL of dry DCM at 0° C. 3-(3-Diethylphosphono-4-diisopropylphosphonomethoxyphenyl)propionic acid (200 mg, 0.42 mmol) in 1.2 mL of dry DMF was added dropwise with stirring. After 5 min, racemic 1-(3-carbamoyl-4-cyclohexylmethoxyphenyl)ethylamine (120 mg, 0.43 mmol) in 0.8 mL of dry DMF was added dropwise. Stirring was continued at 0° C. for 1 hr. The reaction was quenched with 1 mL of saturated NH4Cl, diluted with 17 mL of EtOAc. The organic layer was separated and washed with H2O, 1 N HCl, H2O, 5% NAHCO3, and saturated NH4Cl. The organic layer was dried over Na2SO4 and concentrated to give 253 mg (yield 66%) crude product as an oil.

Workup

  1. stirringStirring
  2. waitwas continued at 0° C. for 1 hr
  3. customThe reaction was quenched with 1 mL of saturated NH4Cl
  4. additiondiluted with 17 mL of EtOAc
  5. customThe organic layer was separated
  6. washwashed with H2O, 1 N HCl, H2O, 5% NAHCO3, and saturated NH4Cl
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-93efecb3bf734bb3ac6e5150c9aa3ccd
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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