Hydrochloric Acid → HCID 136337567, compound

HRID 2224969Notes

Reaction equation

HRID 2224969 reaction equation
C([O:4][CH2:5][C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([C@@:13]1([CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([OH:23])=[C:15]([C:24]2[NH:29][C:28]3[CH:30]=[CH:31][C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])=[CH:33][C:27]=3[S:26](=[O:40])(=[O:39])[N:25]=2)[C:14]1=[O:41])=[O:12])(=O)C.C([O-])([O-])=O.[K+].[K+].Cl>CO>[OH:23][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@:13]([C:11]([N:7]2[CH2:8][CH2:9][CH2:10][C@@H:6]2[CH2:5][OH:4])=[O:12])([CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45])[C:14](=[O:41])[C:15]=1[C:24]1[NH:29][C:28]2[CH:30]=[CH:31][C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])=[CH:33][C:27]=2[S:26](=[O:40])(=[O:39])[N:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 136375609HCID 136375609, compound

Product 1

HCID 136337567HCID 136337567, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 171G (0.15 g, 0.22 mmol) in methanol (2 mL) was added K2CO3 (68 mg, 0.5 mmol). The resulting mixture was stirred at r.t. for 3 hrs, and then poured into N HCl (10 mL), extracted with ethyl acetate (3×10 mL), and the combined organic layers were dried over Na2SO4. The crude product was purified by column chromatography on silica gel using 5% methanol in chloroform, and the title compound was obtained as a lt. yellow solid (0.134 g, 97%). 1H NMR (300 MHz, DMSO-d6): δ 0.45 (m, 1 H), 0.63 (d, J=6.62 Hz, 3 H), 0.69 (d, J=6.62 Hz, 3 H), 0.94 (m, 1 H), 1.27 (m, 1 H), 1.61 (m, 3 H), 1.99 (m, 1 H), 2.23 (m, 2 H), 2.89 (m, 1 H), 3.03 (s, 3 H), 3.20 (m, 1 H), 3.65 (dd, J=9.93, 3.68 Hz, 1 H), 3.98 (m, 1 H), 7.13 (m, 1 H), 7.52 (m, 5 H), 8.11 (m, 1 H), 10.07 (br s, 1 H), 14.18 (br s, 1 H); MS (ESI) m/z=631 [M+H].

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. customThe crude product was purified by column chromatography on silica gel using 5% methanol in chloroform

Sources & evidence

ORD record
ord-ec2ae7d371914b5bbca6111bf62b503d
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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