Nitric Acid → HCID 87666683, compound

HRID 1180621Notes

Reaction equation

[CH3:1][C@H:2]([OH:5])[CH2:3][NH2:4].[N+:6]([O-:9])([OH:8])=[O:7].C(OC(=O)C)(=O)C>>[N+:6]([O-:9])([OH:8])=[O:7].[N+:6]([O:5][C@@H:2]([CH3:1])[CH2:3][NH2:4])([O-:8])=[O:7]

Participants

Reactant 3

HCID 944Nitric Acid2×

HCID 7918Acetic Anhydride

HCID 7311736(S)-(+)-1-Aminopropan-2-ol

Product 1

HCID 87666683HCID 87666683, compound

Procedure

The procedure described for Example 10a was used with S-(+)-1-amino-2-propanol (960 mg, 12.8 mmol), fuming nitric acid (0.62 mL) and acetic anhydride (9.7 ml) and 2.7 mL fuming nitric acid (2.7 ml) to give the title compound as a light green solid in quantitative yield. 1H NMR (CDCl3, 300 MHz) δ 8.08 (s, 3H), 5.32 (m, 1H), 3.24-3.06 (m, 2H), 1.34 (d, J=6.4 Hz, 3H). 13C NMR (CDCl3, 75.45 MHz) δ 78.1, 40.8, 15.9. LRMS (APlMS) m/z 121 (M−HNO3 +H)+.

Sources & evidence

ORD record: ord-f661f7a5b990413bb11e8d93183d051c
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282519B2

Reaction notes

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