Tert-Butyl nitrite → HCID 135543772, compound

HRID 601153Notes

Reaction equation

HRID 601153 reaction equation
N[C:2]1[S:3][C:4]2[C:9]([OH:10])=[C:8]([C:11]3[NH:16][C:15]4[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=4[S:13](=[O:22])(=[O:21])[N:12]=3)[C:7](=[O:23])[N:6]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:5]=2[N:31]=1.N(OC(C)(C)C)=O>CN(C=O)C>[CH2:24]([N:6]1[C:7](=[O:23])[C:8]([C:11]2[NH:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[S:13](=[O:21])(=[O:22])[N:12]=2)=[C:9]([OH:10])[C:4]2[S:3][CH:2]=[N:31][C:5]1=2)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 135457553HCID 135457553, compound

Product 1

HCID 135543772HCID 135543772, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Example 147 (0.0085 g, 0.019 mmol) was reacted with tert-butyl nitrite (5 □L, 0.037 mmol) in DMF (0.3 mL) at 60° C. for 1 hour. The reaction was cooled, and the crude mixture was purified by column chromatography with silica gel eluting with hexane and ethyl acetate (1:1) to give the title compound as a yellow solid (0.0045 g, 54%). MS (ESI) m/z 437 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 5.53 (s, 2 H), 7.25 (m, 1 H), 7.31 (m, 4 H), 7.43 (m, 2 H), 7.66 (m, 1 H), 7.80 (d, J=8.46 Hz, 1 H), 9.48 (s, 1 H), 14.56 (br s, 1 H).

Workup

  1. temperatureThe reaction was cooled
  2. customthe crude mixture was purified by column chromatography with silica gel eluting with hexane and ethyl acetate (1:1)

Sources & evidence

ORD record
ord-fb10eb4b764c4dcfb6f004704db2112c
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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