Nitric Acid → HCID 66869272, compound

HRID 2281858Notes

Reaction equation

HRID 2281858 reaction equation
[CH2:1]([N:3]1[C:8](=[O:9])[C@@H:7]2[C@@H:10]([C:13]([F:16])([F:15])[F:14])[O:11][CH2:12][C@:6]2([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[N:5]=[C:4]1[NH:24]C(=O)OC(C)(C)C)[CH3:2].[OH-].[Na+].[N+:34]([O-])([OH:36])=[O:35]>>[NH2:24][C:4]1[N:3]([CH2:1][CH3:2])[C:8](=[O:9])[C@@H:7]2[C@@H:10]([C:13]([F:14])([F:16])[F:15])[O:11][CH2:12][C@:6]2([C:17]2[CH:22]=[C:21]([N+:34]([O-:36])=[O:35])[CH:20]=[CH:19][C:18]=2[F:23])[N:5]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 69937504HCID 69937504, compound

Product 1

HCID 66869272HCID 66869272, compound

Procedure

tert-Butyl ((4aS,5S,7aS)-3-ethyl-7a-(2-fluorophenyl)-4-oxo-5-(trifluoromethyl)-3,4,4a,5,7,7a-hexahydrofuro[3,4-d]pyrimidin-2-yl)carbamate (300 mg, 0.67 mmol) was taken up in fuming nitric acid (2 mL) at RT. The mixture was stirred at RT for 24 h, then poured on to ice and basified slowly with 50% aq. NaOH (˜3 mL). The aqueous mixture was extracted with DCM (×4). The combined extracts were dried by passing through a hydrophobic frit and then evaporated to give the title compound (200 mg, pale yellow foam). 1H NMR (400 MHz, CDCl3) δ ppm 1.21 (t, J=7.20 Hz, 3H) 3.69-3.80 (m, 1H) 3.83-3.94 (m, 2H) 4.29 (dd, J=8.08, 1.77 Hz, 1H) 4.41-4.50 (m, 2H) 4.67 (br. s., 2H) 7.25 (dd, J=10.61, 9.09 Hz, 1H) 8.23 (ddd, J=8.84, 4.04, 2.78 Hz, 1H) 8.32 (dd, J=6.69, 2.91 Hz, 1H).

Workup

  1. extractionThe aqueous mixture was extracted with DCM (×4)
  2. customThe combined extracts were dried
  3. customevaporated

Sources & evidence

ORD record
ord-e37e403a69594fa0960afd6e795072af
Source dataset
uspto-grants-2015_09
Patent number
US09139594B2

Reaction notes

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