Hydrochloric Acid → HCID 58930573, compound

HRID 416294Notes

Reaction equation

HRID 416294 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:28]=[CH:27][C:12]([O:13][CH2:14][CH2:15][O:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[S:3]1.Cl>CC(O)=O>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][O:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)=[CH:27][CH:28]=2)[S:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58930489HCID 58930489, compound

Product 1

HCID 58930573HCID 58930573, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl ester 359 (872 mg, 2.17 mmol) in glacial AcOH (30 mL) was added conc. HCl (10 mL). The mixture was heated at 120° C. for 3 hours. The solvents were remove under reduced pressure to afford the title compound (833 mg, 99%). 1H NMR: (DMSO-d6) δ (ppm): 12.61 (bs, 1H), 12.01 (s, 1H), 7.91 (d, J=8.8 Hz, 2H), 7.19 (d, J=8.8 Hz, 2H), 7.08 (d, J=8.8 Hz, 2H), 6.95 (d, J=8.8 Hz, 2H), 4.91 (dd, J=9.2, 4.4 Hz, 1H), 4.40-4.42 (m, 2H), 4.33-4.36 (m, 2H), 3.32 (d, J=4.0 Hz, 1H), 3.10 (dd, J=14.0, 9.6 Hz, 1H). LRMS (ESI): (calc.) 387.4; (found) 386.2 (M−H)−.

Workup

  1. customThe solvents were remove under reduced pressure

Sources & evidence

ORD record
ord-e7dff8c268544b81a479d93e828f2a6b
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

Loading…