Ethyl iodoacetate → HCID 58926537, compound

HRID 929626Notes

Reaction equation

HRID 929626 reaction equation
[CH2:1]([N:8]1[C@H:13]([CH3:14])[CH2:12][N:11]([C@H:15]([C:23]2[CH:35]=[CH:34][C:26]([C:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)[C@@H:10]([CH3:36])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:38][C:39]([O:41]CC)=[O:40]>>[CH2:1]([N:8]1[C@H:13]([CH3:14])[CH2:12][N:11]([C@@H:15]([C:16]2[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=2)[O:22][CH2:38][C:39]([OH:41])=[O:40])[C:23]2[CH:24]=[CH:25][C:26]([C:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[O:28])=[CH:34][CH:35]=2)[C@@H:10]([CH3:36])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 12183Ethyl iodoacetateHCID 58619550HCID 58619550, compound

Product 1

HCID 58926537HCID 58926537, compoundYield 84.6%

Procedure

Alkylation of 4-((alpha-R)-alpha-((2S,5R)-4-benzyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide (Example 12) with ethyl iodoacetate, and subsequent hydrolysis of the ester as in Example 14 gave the title compound (84.6%) 1H NMR (0.1-M NaOD in CD3OD, 300 MHz); δ 1.10 (d, J=5.0 Hz, 3H); 1.11 (d, J=5.8 Hz, 3H; both doublets superimposed on m, 3H); 1.23 (m, 3H); 2.03 (m, 2H); 2.57 (m, 2H); 2.69 (m, 2H); 3.30 (m, 3H, superimposed on br m, 2H); 3.88 (d, J=13.1 Hz, 1H); 4.35 (s, 2H); 5.16 (s, 1H): 6.83 (m, 2H); 6.88 (s, 1H); 7.25 (m, 8H); 7.52 (d, J=8.1 Hz, 2H). Mass spectrum: (PFAB, glycerol matrix subtracted): m/z: 544.8, ((M+1)+, 82%).

Sources & evidence

ORD record
ord-e7b2d5a193d74c07ba57c72ed30295be
Source dataset
uspto-grants-2016_03
Patent number
US09296707B2

Reaction notes

Loading…