Methanol → (2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627194Notes

Reaction equation

HRID 627194 reaction equation
CCCCN(C(NC(C1C=C(OC)C(OC)=C(OC)C=1)=[O:14])=S)CCCC.[CH2:27]([O:30][N:31]([CH:44]1[CH2:49][N:48]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:47]([CH2:57][O:58][Si:59]([C:62]([CH3:65])([CH3:64])[CH3:63])([CH3:61])[CH3:60])[CH:46]=[C:45]1[CH2:66][C:67]#[N:68])[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N+:41]([O-:43])=[O:42])(=[O:34])=[O:33])[CH:28]=[CH2:29].C(=NO)C.CO>O>[CH2:27]([O:30][N:31]([CH:44]1[CH2:49][N:48]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:47]([CH2:57][O:58][Si:59]([C:62]([CH3:65])([CH3:64])[CH3:63])([CH3:60])[CH3:61])[CH:46]=[C:45]1[CH2:66][C:67]([NH2:68])=[O:14])[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N+:41]([O-:43])=[O:42])(=[O:34])=[O:33])[CH:28]=[CH2:29]

Participants

6

Reactant 4

HCID 887MethanolHCID 7863AldoximeHCID 12357718N-(dibutylcarbamothioyl)-3,4,5-trimethoxybenzamide2×HCID 89851795(2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(cyanomethyl)-5,6-dihydropyridine-1(2H)-carboxylate2×

Product 1

HCID 89852098(2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4 Å molecular sieves (MS-4 Å) were impregnated with the corresponding metal salt (CuCl2-2H2O) as follows: 1 mmol of the salts was dissolved in 100 ml of deionized H2O and stirred with 1 g of MS-4 Å at room temperature for 6 h. The solid was filtered, washed with deionized H2O and acetone, and dried in an oven at 150° C. for 1 h. (2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(cyanomethyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 172, 3.60 g, 5.78 mmol), Cu(II)Cl2-4 Å catalyst (200 mg), acetaldoxime (1.762 mL, 28.90 mmol, 5.0 eq) and MeOH (40.0 mL) were stirred at 60° C. for 15 h. The solid was filtered, washed with MeOH and the filtrate was evaporated to afford crude product.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with deionized H2O and acetone
  3. filtrationThe solid was filtered
  4. washwashed with MeOH
  5. customthe filtrate was evaporated
  6. customto afford crude product

Sources & evidence

ORD record
ord-5f54397545a64955978ee5a24fcd2daf
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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