3-[4-Hydroxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester → 3-{2-(Isopropoxycarbonylamino-methyl)-4-[2-(5-methyl-2-morpholin-4-yl-thiazol-4-yl)-ethoxy]-phenyl}-propionic acid tert-butyl ester

HRID 1181058Notes

Reaction equation

HRID 1181058 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][NH:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]1[S:30][C:29]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[N:28][C:27]=1[CH2:37][CH2:38]OS(C1C=CC(C)=CC=1)(=O)=O>>[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:38][CH2:37][C:27]2[N:28]=[C:29]([N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)[S:30][C:26]=2[CH3:25])=[CH:11][C:10]=1[CH2:16][NH:17][C:18]([O:20][CH:21]([CH3:22])[CH3:23])=[O:19])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 589794703-[4-Hydroxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl esterHCID 59785947Toluene-4-sulfonic acid 2-(5-methyl-2-morpholin-4-yl-thiazol-4-yl)-ethyl ester

Product 1

HCID 589792873-{2-(Isopropoxycarbonylamino-methyl)-4-[2-(5-methyl-2-morpholin-4-yl-thiazol-4-yl)-ethoxy]-phenyl}-propionic acid tert-butyl esterYield 98%

Procedure

3-[4-hydroxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester (272 mg, 0.806 mmol) and toluene-4-sulfonic acid 2-(5-methyl-2-morpholin-4-yl-thiazol-4-yl)-ethyl ester (522 mg, 1.36 mmol) were reacted according to Standard procedure A. Purification using radial chromatography (CH2Cl2/EtOAc 98:2 to 75:25) gave the title compound as a white solid (387 mg, 98%). 1H NMR (400 MHz, CDCl3) δ 1.14 (d, 6H, J=5.9 Hz), 1.32 (s, 9H), 2.16 (s, 3H), 2.39 (t, 2H, J=7.6 Hz), 2.77 (t, 2H, J=7.6 Hz), 2.84 (t, 2H, J=7.1 Hz), 3.28 (t, 4H, J=4.9 Hz), 3.70 (t, 4H, J=4.9 Hz), 4.08 (t, 2H, J=7.1 Hz), 4.25 (d, 2H, J=5.4 Hz), 4.83 (heptet, 1H, J=4.9 Hz), 6.66 (dd, 1H, J=2.4, 8.3 Hz), 6.72 (d, 1H, J=2.4 Hz), 6.98 (d, 1H, J=8.3 Hz). MS (ES) m/e 548.3 [M+1].

Workup

  1. customPurification

Sources & evidence

ORD record
ord-5c7fbdac3326425284b582bfbd9ef724
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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