Diethyl Ether → HCID 86643607, compound

HRID 2381039Notes

Reaction equation

HRID 2381039 reaction equation
[Cl-:1].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([NH3+:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:4]=1[O:16][C:17](=[O:20])[NH:18][CH3:19].[CH2:21]([O:23]CC)[CH3:22]>C(O)(=O)C>[Cl-:1].[C:21]([O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([NH3+:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:4]=1[O:16][C:17](=[O:20])[NH:18][CH3:19])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 86643599HCID 86643599, compound

Product 1

HCID 86643607HCID 86643607, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(S)-2-(4-Hydroxy-3-methylcarbamoyloxyphenyl)-1-methoxycarbonylethylammonium chloride (1.68 g, 6.26 mM) was dissolved in acetic acid (25 ml). HCl (g) was bubbled through the reaction mixture for 5 minutes before adding acetyl chloride (4.45 ml, 62.6 mM) dropwise. The reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated to approximately half of its initial reaction volume. Diethyl ether was added to afford a solid. The solvent was evaporated and the residue was triturated with diethyl ether. The product was collected by filtration and dried under vacuum to constant weight to afford (S)-2-(4-Acetoxy-3-methylcarbamoyloxy-phenyl)-1-methoxycarbonyl-ethyl-ammonium chloride as a solid, 1.55 g. 1H-NMR (500 MHz, DMSO-d6): δ=2.23 (s, 3H), 2.65 (d, J=4.6 Hz, 3H), 3.08-3.11 (m, J=14.35 Hz, 7.1 Hz, 1H), 3.14-3.17 (m, J=14.15 Hz, 5.9 Hz, 1H), 3.68 (s, 3H), 4.28 (t, 1H, CH), 7.10-7.17 (m, 3H), 7.70 (q, J=4.55 Hz, 1H), 8.59 (s, 3H). HPLC/MS (Method A) retention time 2.85 min, m/z 311 (MH+).

Workup

  1. customHCl (g) was bubbled through the reaction mixture for 5 minutes
  2. additionbefore adding acetyl chloride (4.45 ml, 62.6 mM) dropwise
  3. concentrationThe mixture was concentrated to approximately half of its initial
  4. customreaction volume
  5. customto afford a solid
  6. customThe solvent was evaporated
  7. customthe residue was triturated with diethyl ether
  8. filtrationThe product was collected by filtration
  9. customdried under vacuum to constant weight

Sources & evidence

ORD record
ord-3c2bd40d1e08442280d706005523f54f
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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