tert-Butyl Crotonate → HCID 86755228, compound

HRID 1637040

Reaction equation

HRID 1637040 reaction equation
C(OC(C)(C)C)(=O)/C=C/C.[CH3:11][C@H:12]([NH:19][C@H:20]([C:29]1C=CC=C[CH:30]=1)[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N([C@@H](C)C1C=CC=CC=1)[C@@H](C=CC)CC(OC(C)(C)C)=O)C=C.CC(C)C=CC(OC(C)(C)C)=O.C(N([C@@H](C)C1C=CC=CC=1)[C@@H](C=CC1C=CC=CC=1)CC(OC(C)(C)C)=O)C=C>C(Cl)(Cl)Cl>[CH3:11][C@H:12]([NH:19][C@@H:20]([CH2:29][CH3:30])[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 5463127tert-Butyl CrotonateHCID 15344490HCID 15344490, compoundHCID 53938938tert-Butyl 4-methylpent-2-enoateHCID 86755224HCID 86755224, compoundHCID 86755229HCID 86755229, compound

Product 1

HCID 86755228HCID 86755228, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The title compound (31) was prepared from compound (10) of Example 3 using the above-described procedure. [α]D21 -54.0 (c 1.81, CHCl3); νmax (CHCl3)/cm-1 1724 s (C=O); δH (300 MHz; CDCl3) 7.36-7.20 (5H, m, Ph), 3.91 (1H, q, J=6.5, PhCHCH3), 2.68 (1H, m, NCHCH2), 2.39, 2.28 (2H, ABX system, JAB =14.3, JAX =5.7, JBX =5.5, CH2CO), 1.47 (9H, s, (CH3)3C), 1.41 (2H, m, CH3CH2), 1.34 (3H, d, J=6.5, PhCHCH3), 0.85 (3H, t, J=7.3, CH3CH2); δC (50 MHz; CDCl3) 172.19 (C=O), 146.44, (Ph:Cipso), 128.53, 126.92 (Ph:Cortho, Cmeta), 126.84 (Ph:Cpara), 80.23 (C(CH3)3), 55.01, 53.71 (CHN), 39.10 (CH2CO), 28.04 (C(CH3)3), 27.78 (CH3CH2), 24.80 (NCHCH3), 10.24 (CH3CH2); m/z (CI) 278 (MH+, 100%), 248 (5), 222 (30), 192 (12), 162 (15), 105 (20); (Found: C, 73.84; H, 10.11; N, 4.93. C17H27NO2 requires C, 73.61; H, 9.81; N, 5.05%).

Sources & evidence

ORD record
ord-bc1aabb183e74b0fa553309505b2eb52
Source dataset
uspto-grants-2000_03
Patent number
US06037498

Linked notes

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