3-{4-[4-(Tert-butoxycarbonylaminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionic acid → 3-{4-[4-(Aminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionic acid

HRID 749008Notes

Reaction equation

C(OC([NH:8][CH:9]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[C:10]1[CH:27]=[CH:26][C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1)=O)(C)(C)C>C(Cl)Cl>[NH2:8][CH:9]([C:28](=[O:32])[N:29]([CH3:30])[CH3:31])[C:10]1[CH:27]=[CH:26][C:13]([O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:19][CH:20]=2)=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

The acid compound 33 (0.3 g) was dissolved in CH2Cl2 (20 mL) and cooled to 0-5° C. Hydrogen chloride gas was bubbled through this solution for 20 min. The bubbling was discontinued and the reaction mixture was stirred at room temp for 1 h. The excess HCl was degassed and the CH2Cl2 was removed. The residual solid was triturated with EtOAc (2×25 mL), decanted, and dried to yield the desired compound 37 as a white amorphous solid (0.15 g, 59%). 1H NMR (400 MHz, DMSO-d6): 12.2 (br, 1H), 7.47 (d, J=9.2 Hz, 2H), 7.29 (d, J=8.4 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 6.96 (d, J=8.4 Hz, 2H), 5.49 (s, 1H), 2.90 (s, 3H), 2.81-2.84 (m, 5H), 2.54 (t, J=8.0 Hz, 2H).

Workup

customHydrogen chloride gas was bubbled through this solution for 20 min
customThe excess HCl was degassed
customthe CH2Cl2 was removed
customThe residual solid was triturated with EtOAc (2×25 mL)
customdecanted
customdried

Sources & evidence

ORD record: ord-261f774d7eb04d2aae13da042cf248ec
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399786B2

Reaction notes

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