Methyl 4-aminobenzoate → Tert-butyl 2-(4-(cyclopentanecarboxamido)benzamido)-3-(4-hydroxy-3-methoxyphenyl)propanoate

HRID 1889163Notes

Reaction equation

HRID 1889163 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[CH:4][CH:3]=1.[CH:12]1([C:17](Cl)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]1.[NH2:20][CH:21]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([O:37][CH3:38])[CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>>[CH:12]1([C:17]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([NH:20][CH:21]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([O:37][CH3:38])[CH:31]=3)[C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[O:8])=[CH:10][CH:11]=2)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 78284Cyclopentanecarbonyl chlorideHCID 58545613Tert-butyl 2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoate

Product 1

HCID 58545808Tert-butyl 2-(4-(cyclopentanecarboxamido)benzamido)-3-(4-hydroxy-3-methoxyphenyl)propanoate

Procedure

Prepared using General Procedures 5, 12 and 6 starting from methyl 4-aminobenzoate and using cyclopentane carbonyl chloride and tert-butyl 2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoate. LCMS-ESI (m/z) calculated for C27H34N2O6: 482; found 505, [M+Na]+, tR=3.21 min (Method 1). NMR (400 MHz, CDCl3) δ 7.79-7.67 (m, 2H), 7.60 (d, J=8.7 Hz, 2H), 6.88-6.75 (m, 1H), 6.73-6.60 (m, 2H), 6.56 (d, J=7.4 Hz, 1H), 5.52 (s, 1H), 4.89 (ddd, J=7.3, 6.1, 5.0 Hz, 1H), 3.76 (s, 3H), 3.16 (m, 2H), 2.69 (m, 1H), 2.01-1.85 (m, 4H), 1.80 (m, 2H), 1.69-1.58 (m, 2H), 1.46 (s, 9H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c2b29fdec3754b6294f82cc2b73ef573
Source dataset
uspto-grants-2013_08
Patent number
US08501982B2

Reaction notes

Loading…