t-Butyl pentadienoate → (3R,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)-3-(fur-2-yl)propionate

Participants

Role	Name	HCID	Charge
Reactant	t-Butyl pentadienoate	HCID 53950126	—
Reactant	(3R,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-5-phenyl-4-pentenoate	HCID 86755224	—
Reactant	(2S,3S,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-2-hydroxy-3-phenylpropionate	HCID 86755227	—
Reactant	(3R,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-3-(fur-2-yl)-propionate	HCID 86755232	—
Solvent	Chloroform	HCID 6212	—
Product	(3R,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)-3-(fur-2-yl)propionate	HCID 86755231	—

Reaction Steps

The title compound (33) was prepared from compound (14) of Example 5 using the above-described procedure. [α]D21 -1.5 (c 1.74, CHCl3); νmax (CHCl3)/cm-1 1729 s (C=O); δH (300 MHz; CDCl3) 7.32-7.20 (6H, m, Ph, OCH=CH), 6.28 (1H, dd, J=3.2 and 1.9, OCH=CH), 6.15 (1H, d, J=3.2, OCH=CH), 4.19 (1H, t, J=6.9, NCHCH2), 3.76 (1H, q, J=6.5, PhCHCH3); δC (50 MHz; CDCl3) 170.93 (C=O), 156.00 (OC=CH), 146.15 (Ph:Cipso), 141.78 (OCH=CH), 128.61, 126.81 (Ph:Cortho, Cmeta), 127.14 (Ph:Cpara), 110.10 (OCH=CH), 106.40 (OC=CH), 80.55 (C(CH3)3), 54.97, 50.83 (CHN), 40.72 (CH2CO), 27.96 (C(CH3)3), 23.04 (NCHCH3); m/z (CI) 316 (MH+, 100%), 260 (25), 200 (25), 154 (20), 120 (25), 105 (27); (Found: C, 72.37; H, 8.04; N, 4.31. C19H25NO3 requires C, 72.35; H, 7.99; N, 4.44%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06037498
Source dataset	uspto-grants-2000_03
ORD ID	ord-115000730bdb4be59ad8ee951013d785
Source note	uspto-grants-2000_03