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Hydrochloric Acid → HCID 57978659, compound

HRID 1866862
Notes
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Reaction equation

HRID 1866862 reaction equation
[CH3:1]C1C=CC(S(O)(=O)=O)=CC=1.[C:12]1([C:18]2([C:25]3[CH:34]=[C:33]([O:35][CH2:36][C:37]4[CH:46]=[CH:45][C:44]5[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=5)[N:38]=4)[CH:32]=[CH:31][C:26]=3[C:27]([NH:29][NH2:30])=[O:28])[CH2:23][CH:22]3[CH2:24][CH:19]2[CH2:20][CH2:21]3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.C(=O)(O)[O-].[Na+]>C(OC(OCC)OCC)C>[O:28]1[CH:1]=[N:30][N:29]=[C:27]1[C:26]1[CH:31]=[CH:32][C:33]([O:35][CH2:36][C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]=2)=[CH:34][C:25]=1[C:18]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:23][CH:22]2[CH2:24][CH:19]1[CH2:20][CH2:21]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 57978651HCID 57978651, compound

Product 1

HCID 57978659HCID 57978659, compound

Reagents, catalysts & solvents 1

HCID 31214
Ethyl orthoformate
Solvent

Procedure

A catalytic amount of p-TSA (˜3 mg) was added to a stirred suspension of 4d HCl salt (54.6 mg, 0.10 mmol) in triethylorthoformate (600 μL) at room temperature. After 30 min, 1N hydrochloric acid (600 μL) was added, and the resulting solution was aged for an additional 45 min. The reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (gradient elution; 0-75% acetonitrile/water as eluent, 0.1% TFA as modifier). Lyophilization of the purified fractions afforded the title compound Sc, m/z (ES) 474 (MH)+.

Workup

  1. waitthe resulting solution was aged for an additional 45 min
  2. extractionextracted three times with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (gradient elution; 0-75% acetonitrile/water as eluent, 0.1% TFA as modifier)

Sources & evidence

ORD record
ord-ca94dbd98376458c9bd4b46278dec6fd
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07629467B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes