N-chlorosuccinamide → tert-Butyl N-(4-{1-[1-(3-chloro-4-methoxyphenyl)-3-oxopropyl]pentyl}benzoyl)-beta-alaninate

HRID 2427802Notes

Reaction equation

HRID 2427802 reaction equation
[Cl:1]NC(=O)CCC(N)=O.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH:22]([C:27]2[CH:44]=[CH:43][C:30]([C:31]([NH:33][CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:32])=[CH:29][CH:28]=2)[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH:20]=[O:21])=[CH:14][CH:13]=1>C(#N)C>[Cl:1][C:17]1[CH:16]=[C:15]([CH:18]([CH:22]([C:27]2[CH:28]=[CH:29][C:30]([C:31]([NH:33][CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:32])=[CH:43][CH:44]=2)[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH:20]=[O:21])[CH:14]=[CH:13][C:12]=1[O:11][CH3:10]

Participants

4

Reactant 2

HCID 15238416N-chlorosuccinamideHCID 86619552tert-butyl N-(4-{1-[1-(4-methoxyphenyl)-3-oxopropyl]pentyl}benzoyl)-beta-alaninate

Product 1

HCID 86619551tert-Butyl N-(4-{1-[1-(3-chloro-4-methoxyphenyl)-3-oxopropyl]pentyl}benzoyl)-beta-alaninate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Chlorosuccinamide (40 mg, mmol) was added to an acetonitrile solution (2 ml) containing enantiopure tert-butyl N-(4-{1-[1-(4-methoxyphenyl)-3-oxopropyl]pentyl}benzoyl)-β-alaninate (20 mg, 0.42 mol), which was prepared following the procedure described in Example 1. The solution was then heated in a screw cap tube for 35 minutes at 85° C. The solution was concentrated and the residue purified by PTLC using an EtOAC/hexanes eluent to give a mixture of compounds containing the title compound and the corresponding 3,5-diCl analog (˜30% by NMR). LC1 4.00 min. (M+H) 460, di Cl LC1 4.15 min. (M+H) 494 selected data 1H NMR (400 MHz, CDCl3): δ 9.35 (s, 1H); 7.72 (d, J=8.2 Hz, 2H); 7.23-7.15 (m, 3H); 6.86 (d, J=8.4 Hz, 2H); 3.88 (S, 3H); 3.68 (q, J=5.9 Hz, 2H); 3.29-3.23 (m, 1H); 2.75-2.65 (m, 1H); 2.56-2.50 (m, 2H); 2.39-2.31 (m, 1H); 1.46 (s, 9H); 0.66 (t, 3H).

Workup

  1. customwas prepared
  2. temperatureThe solution was then heated in a screw
  3. customcap tube for 35 minutes at 85° C
  4. concentrationThe solution was concentrated
  5. customthe residue purified by PTLC
  6. customto give
  7. additiona mixture of compounds

Sources & evidence

ORD record
ord-5d6c51624e6c41f88710e71c942a5110
Source dataset
uspto-grants-2011_06
Patent number
US07968589B2

Reaction notes

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