Hydrochloric Acid → HCID 22220122, compound

HRID 1794100Notes

Reaction equation

HRID 1794100 reaction equation
Cl.O1CCOCC1.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[S:40])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32](=[O:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:26][CH:25]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(OCC)(=O)C>[N:18]1([C:21](=[S:40])[O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH2:31][C:32](=[O:39])[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[CH:28][CH:29]=2)[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 22219935HCID 22219935, compound

Product 1

HCID 22220122HCID 22220122, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

a solution of HCl in dioxane (4 M; 380 uL, 10 eq) was added to a solution of 4-(2-oxo-2-phenylethoxy)benzyl 4-tert-butoxycarbonylpiperazine-1-thiocarboxylate (72.1 mg) in ethyl acetate (2 mL) and the resultant mixture was shaken at ambient temperature for 16 h. The solvent was removed in vacuo and the resultant crude material was suspended in dichloromethane (4 mL) and shaken with MP—CO3 (1 g, 17 eq) at ambient temperature for 1 h. Purification by ion-exchange chromatography [SCX-2 (500 mg); DCM, MeOH, NH3—MeOH] afforded the desired product (44.7 mg, 79%) as a colourless oil: NMR δH(400 MHz; CDCl3) 2.82–2.86 (4H, m), 3.41–3.63 (4H, br s), 4.12 (2H, s), 5.23 (2H, s), 6.84–6.90 (2H, m), 7.24–7.29 (2H, m), 7.46–7.52 (2H, m) and 7.58–7.64 (1H, m); HPLC (XTERRA, 50/80, 235 nm) 97.7% (2.05 min).

Workup

  1. customThe solvent was removed in vacuo
  2. customPurification by ion-exchange chromatography [SCX-2 (500 mg); DCM, MeOH, NH3—MeOH]

Sources & evidence

ORD record
ord-15c636ba39684fd6848c305b6f3a1448
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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