Hydrogen Peroxide → HCID 59287354, compound

HRID 1994529Notes

Reaction equation

HRID 1994529 reaction equation
C([C@@H]1COC(=O)N1C(=O)[C@@H:15]([CH3:29])[C@@H:16]([OH:28])[C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=1[I:27])C1C=CC=CC=1.[OH-:31].[Li+].OO.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:54]([CH2:57]C)CC)C>>[I:27][C:18]1[CH:19]=[CH:20][C:21]([C:23]([F:24])([F:25])[F:26])=[CH:22][C:17]=1[C@@H:16]1[O:28][C:57](=[O:31])[NH:54][C@H:15]1[CH3:29]

Participants

6

Reactant 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59135219HCID 59135219, compound

Product 1

HCID 59287354HCID 59287354, compound

Procedure

Following the procedure described in EXAMPLE 95, Step B, 0.214 g of (4R)-4-benzyl-3-{(2S,3R)-3-hydroxy-3-[2-iodo-5-(trifluoromethyl)phenyl]-2-methylpropanoyl}-1,3-oxazolidin-2-one, 0.034 g of lithium hydroxide, 0.16 mL of a 30% aqueous solution of hydrogen peroxide, 0.1 mL of diphenylphosphoryl azide, and 0.072 mL of triethylamine provide the title compound. Mass spectrum (ESI) 372.1 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.02 (d, J=8 Hz, 1H), 7.61 (d, J=1.5 Hz, 1H), 7.32 (dd, J=2 Hz, 8 Hz, 1H), 6.16 (s, 1H), 5.39 (d, J=4 Hz, 1H), 3.76 (dq, J=6 Hz, 4.5 Hz, 1H), 1.62 (d, J=6 Hz, 3H). Analytical HPLC on Chiralpak AD 4.6×250 mm, eluting with 4% ethanol in heptane at 0.75 mL/min (tR=21.56 min for R,R; tR=18.00 min for S,S) showed 99% e.e.

Sources & evidence

ORD record
ord-d4a9c3eba8fc4e68af3fce1519e643b7
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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