Hydrochloric Acid → HCID 178488092, compound

HRID 1174610Notes

Reaction equation

HRID 1174610 reaction equation
O[Li].O.C[O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:17]=3[N:16]=2)[SH:14])=[CH:9][CH:8]=1.Cl>O.C1COCC1>[CH3:25][O:24][C:22]1[CH:21]=[CH:20][C:18]2[NH:19][C:15]([CH:13]([SH:14])[C:10]3[CH:11]=[CH:12][C:7]([C:6]([OH:26])=[O:5])=[CH:8][CH:9]=3)=[N:16][C:17]=2[CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 178498015HCID 178498015, compound

Product 1

HCID 178488092HCID 178488092, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH.H2O (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, 3 H). 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-08a973da1c954aa5a039fe2c82519055
Source dataset
uspto-grants-2010_11
Patent number
US07838520B2

Reaction notes

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