Hydrochloric Acid → HCID 59447540, compound

HRID 1518418Notes

Reaction equation

HRID 1518418 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10](COCC[Si](C)(C)C)[C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31]C(C)(C)C)=[O:30])[C:26]([CH2:36][CH2:37][CH2:38][O:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].O.Cl>CCO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([OH:31])=[O:30])[C:26]([CH2:36][CH2:37][CH2:38][O:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 59447462HCID 59447462, compound

Product 1

HCID 59447540HCID 59447540, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Compound 121E (55 mg, 0.073 mmol) was dissolved in 1 mL of EtOH. Water (1 mL) was added followed by 1 mL of concentrated HCl. The reaction was stirred at 50° C. for 12 hours. The solids that precipitated were collected by filtration and rinsed with water. The solid was purified by preparative HPLC to give a white solid: 1H NMR (300 MHz, DMSO-d6) δ2.09 (t, 2H), 3.06 (t, 2H), 3.21 (t, 2H), 3.91 (t, 2H), 3.97 (t, 2H), 5.21 (s, 2H), 6.87-6.94 (m, 4H), 7.25-7.42 (m, 5H), 7.46-7.50 (m, 2H), 7.56 (m, 1H), 8.01 (m, 1H); LCMS m/z 565.7 (M+1).

Workup

  1. customThe solids that precipitated
  2. filtrationwere collected by filtration
  3. washrinsed with water
  4. customThe solid was purified by preparative HPLC
  5. customto give a white solid

Sources & evidence

ORD record
ord-86b7e8f979a7406ca1d74af53e388bc1
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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