(3S,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)-3-phenylpropionate → (3R,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)-4-hexenoate

HRID 1637041Notes

Reaction equation

HRID 1637041 reaction equation
C([N:4]([C@@H:17]([CH3:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:5]([CH:14]=[CH:15][CH3:16])[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])C=C.C[C@H](N[C@H](C1C=CC=CC=1)CC(OC(C)(C)C)=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:24][C@H:17]([NH:4][C@@H:5]([CH:14]=[CH:15][CH3:16])[CH2:6][C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 15344490(3S,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)-3-phenylpropionateHCID 86755229(3R,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-4-hexenoate

Product 1

HCID 86755230(3R,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)-4-hexenoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The title compound (32) was prepared from compound (12) of Example 4 using the above-described procedure. [α]D21 -45.1 (c 1.69, CHCl3); νmax (CHCl3)/cm-1 1728 s (C=O); δH (300 MHz; CDCl3) 7.32-7.18 (5H, m, Ph), 5.55 (1H, dq, J=15.2 and 6.4, CH3CH=CH), 5.26 (ddq, J=15.2, 8.0 and 1.6, CH3CH=CH), 3.84 (1H, q, J=6.5, PhCHCH3), 3.45 (1H, m, NCHCH2), 2.41, 2.35 (2H, ABX system, JAB =14.5, JAX =6.6, JBX =6.5, CH2CO), 1.65 (3H, dd, J=6.4 and 1.6, CH3C=C), 1.45 (9H, s, (CH3)3C), 1.33 (3H, d, J=6.5, PhCHCH3); δC (50 MHz; CDCl3) 171.53 (C=O), 146.51 (Ph:Cipso), 133.07 (CH3C=C), 128.53, 126.82 (Ph:Cortho, Cmeta), 126.96 (Ph:Cpara), 80.28 (C(CH3)3), 55.14, 54.57 (CHN), 41.78 (CH2CO), 28.03 (C(CH3)3), 23.12 (NCHCH3), 17.83 (CH3C=C); m/z (CI) 290 (MH+, 100%), 234 (30), 174 (45), 105 (35); (Found: C, 74.61; H, 9.63; N, 4.62. C18H27NO2 requires C, 74.70; H, 9.40; N, 4.84%).

Sources & evidence

ORD record
ord-7b755e9071f942b3a8f92da38218a6e7
Source dataset
uspto-grants-2000_03
Patent number
US06037498

Reaction notes

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