HCID 13812516, compound → HCID 59567461, compound

HRID 2098304Notes

Reaction equation

HRID 2098304 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@:4]([N:15]=[C:16]=[O:17])([CH3:14])[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[N+:19](=[C:21]1[N:25]=[CH:24][N:23]=[C:22]1[C:26]([NH2:28])=[O:27])=[N-:20]>CS(C)=O>[CH3:1][O:2][C:3](=[O:18])[C@:4]([N:15]1[C:16](=[O:17])[N:25]2[CH:24]=[N:23][C:22]([C:26](=[O:27])[NH2:28])=[C:21]2[N:19]=[N:20]1)([CH3:14])[CH2:5][O:6][Si:7]([C:10]([CH3:11])([CH3:12])[CH3:13])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 13812516HCID 13812516, compoundHCID 534265854-Diazo-4H-imidazole-5-carboxamide

Product 1

HCID 59567461HCID 59567461, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (S)-3-(tert-butyl-dimethyl-silanyloxy)-2-isocyanato-2-methyl-propionic acid methyl ester (510 mg, 1.86 mmol) in dry DMSO (1.5 mL) was added 5-diazoimidazole-4-carboxamide (135 g, 0.98 mmol) at room temperature under nitrogen. The reaction mixture was stirred for 2 hours whereupon it was poured onto crushed ice. The resultant white precipitate was collected by vacuum filtration. The filter cake was washed with water (2×1 reaction volume), EtOAc (1 reaction volume) and then Et2O (1 reaction volume) to give (S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(8-carbamoyl-4-oxo-imidazo[5,1-d][1,2,3,5]tetrazin-3-yl)-2-methyl-propionic acid methyl ester as a pale off white solid (140 mg, 34%). 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.96 (CH, s, 1H), 7.91 (CONH2, s, 1H), 7.77 (CONH2, s, 1H), 5.77 (CH, dd, J=8.8 Hz, 5.6 Hz, 1H), 4.36 (CH2, dd, J=10.6 Hz, 5.6 Hz, 1H), 4.23 (CH2, dd, J=10.6 Hz, 8.8 Hz, 1H), 3.72 (CO2CH3, s, 3H), 0.72 (SiC(CH3)3, s, 9H), 0.03 (SiCH3, s, 3H), −0.06 (SiCH3, s, 3H).

Workup

  1. additionwas poured
  2. customonto crushed ice
  3. filtrationThe resultant white precipitate was collected by vacuum filtration
  4. washThe filter cake was washed with water (2×1 reaction volume), EtOAc (1 reaction volume)

Sources & evidence

ORD record
ord-b3fbc4b058734dbfba4c3c2cd8d5b7e4
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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