Hydrochloric Acid → HCID 178488092, compound

HRID 736509Notes

Reaction equation

HRID 736509 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:25])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:16]=3[N:15]=2)[SH:13])=[CH:8][CH:7]=1.Cl>O.C1COCC1>[CH3:24][O:23][C:21]1[CH:20]=[CH:19][C:17]2[NH:18][C:14]([CH:12]([SH:13])[C:9]3[CH:10]=[CH:11][C:6]([C:5]([OH:25])=[O:4])=[CH:7][CH:8]=3)=[N:15][C:16]=2[CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178498015HCID 178498015, compound

Product 1

HCID 178488092HCID 178488092, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH.H20 (1.02 g, 24.4 mmol) in water (15 ml) was added to a suspension of 376a (3.99 g, 9.75 mmol of in THF (10 ml). The reaction mixture was stirred 16 h at room temperature. The reaction mixture was acidified with a solution of HCl 1 M to pH 4. The desired product was triturated 20 min. at 0° C. and then filtered and dried. Compound 376b was obtained as a white powder (100% yield, 3.05 g). 1H NMR: (DMSO) δ (ppm): 12.85 (bs, 1H), 7.86 (d, J=8.1 Hz, 2H), 7.53 (d, J=8.1 Hz, 2H), 7.35 (d, J=8.1 Hz, 1H), 6.97 (d, J=2.2 Hz, 1H), 6.76 (dd, J=8.8, 2.2 Hz, 1H), 4.60 (s, 2H), 3.82 (s, 3H). MS: (calc.) 314.1, (obt.), 315.1 (MH)+.

Workup

  1. customThe desired product was triturated 20 min. at 0° C.
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-88354d9a8f8b43d8a2c0c8d2d3a76070
Source dataset
uspto-grants-2009_09
Patent number
US07595343B2

Reaction notes

Loading…