Hydrochloric Acid → HCID 178425709, compound

HRID 2121248Notes

Reaction equation

HRID 2121248 reaction equation
C[O:2][C:3](=[O:37])[C@H:4]([CH2:6][CH:7]([C:10](=[O:36])[C:11]1[CH:16]=[CH:15][C:14](=[CH2:17])[CH:13]([NH:18][C:19]2[N:20]=[C:21]([CH:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH2:25]3)[NH:22][CH:23]=2)[C:12]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[S:8][CH3:9])[NH2:5].[OH-].[Li+].Cl>C1COCC1>[CH:24]1([C:21]2[NH:22][CH:23]=[C:19]([NH:18][CH:13]3[C:14](=[CH2:17])[CH:15]=[CH:16][C:11]([C:10]([CH:7]([S:8][CH3:9])[CH2:6][C@@H:4]([C:3]([OH:37])=[O:2])[NH2:5])=[O:36])=[C:12]3[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:20]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH2:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178425708HCID 178425708, compound

Product 1

HCID 178425709HCID 178425709, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 382A (0.1 g, 0.19 mmol) was dissolved into 2 mL. of THF and cooled to 0° C. Lithium hydroxide (2 mLs, 0.5M) was slowly added to the reaction mixture and stirred for 3 Hrs. The pH was adjusted using 0.5 M HCl and a white precipitate was collected by vacuum filtration and purified twice by reverse phase preparative HPLC (Waters 25×10 cm, C-18 column, 220 nm UV detector, flow rate 15 mLs/min, linear gradient from 5% acetonitrile and 95% water containing 0.1% TFA to 60% acetonitrile in 40 minutes). Fractions containing pure compound were combined and lyophilized to yield the title compound (0.021 g, 18%) as a TFA salt: 1H NMR (300 MHz, methanol-d4) δ 8.04 (d, J=7.8 Hz, 1H), 7.79 (dd, J=7.3 Hz, 2H), 7.60-7.62 (m, 4H), 7.27-7.30 (m, 6H), 6.69 (dd, J=8.4 Hz, 1H), 6.63 (d, J=2.1, 1H) 4.42 (s, 2H), 4.19-4.26 (m, 1H), 2.14-2.32 (m, 2H), 1.98 (s, 3H), 1.75-1.87 (m, 2H).

Workup

  1. filtrationa white precipitate was collected by vacuum filtration
  2. custompurified twice by reverse phase preparative HPLC (Waters 25×10 cm, C-18 column, 220 nm UV detector, flow rate 15 mLs/min, linear gradient from 5% acetonitrile and 95% water containing 0.1% TFA to 60% acetonitrile in 40 minutes)
  3. additionFractions containing pure compound

Sources & evidence

ORD record
ord-8122510372674dbfafb0337bea2f0d85
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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