Water → tert-butyl ((3E)-4-cyano-3-[({5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl}amino)carbonyl]-3-buten-1-yl}carbamate

HRID 459630Notes

Reaction equation

HRID 459630 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].O=[C:15]([C:26](=[O:75])[NH:27][C:28]1[CH:29]=[N:30][N:31]([CH2:53][CH2:54][O:55][C:56]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:32]=1[NH:33][C:34]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].O>O1CCCC1>[C:1](/[CH:3]=[C:15](/[C:26]([NH:27][C:28]1[CH:29]=[N:30][N:31]([CH2:53][CH2:54][O:55][C:56]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[C:32]=1[NH:33][C:34]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:75])\[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 86597882tert-butyl [3,4-dioxo-4-({5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl}amino)butyl]carbamate

Product 1

HCID 86597883tert-butyl ((3E)-4-cyano-3-[({5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl}amino)carbonyl]-3-buten-1-yl}carbamateYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of diethyl (cyanomethyl)phosphonate (311 mg) in tetrahydrofuran (13 ml) was added sodium hydride (70.3 mg, 60% oil suspension) under nitrogen atmosphere at 0° C., and the mixture was stirred for 45 minutes with warming to room temperature. tert-Butyl [3,4-dioxo-4-({5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl}amino)butyl]carbamate (1.32 g) was added to the mixture and the stirring was continued for 30 minutes. Water was added to the reaction mixture and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave tert-butyl {(3E)-4-cyano-3-[({5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl}amino)carbonyl]-3-buten-1-yl}carbamate (1.13 g).

Workup

  1. waitthe stirring was continued for 30 minutes
  2. extractionthe whole mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-d6ef255a90434cc3abc6201b85dd6919
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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