Hydrochloric Acid → HCID 54444285, compound

HRID 263505Notes

Reaction equation

HRID 263505 reaction equation
C([S:4][C@@H:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@H:6]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]([O:9][CH3:10])=[O:8])(=O)C.[OH-].[Na+].Cl>CO>[C:15]([O:14][C:12]([NH:11][C@@H:6]([C@@H:5]([SH:4])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15747429HCID 15747429, compound

Product 1

HCID 54444285HCID 54444285, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The acetylated thiol 7 (290 mg, 0.82 mmol) was dissolved in methanol (4 mL) and NaOH was added (4.1 mL, 0.2N aqueous). The reaction was stirred at room temperature for 20 min (monitored by TLC). The solution was then carefully neutralized with dilute HCl. The volatiles were removed in vacuo and the residue was extracted with Cl2CH2 (3×). The organic layer was washed with brine and dried over Na2SO4. The crude product was purified by flash column chromatography (silica, 10% ethyl acetate/hexane) to give the desired thiol 9 (242 mg, 95%) as a white solid. mp 76°-77° C. (ether-hexane); [α]20D =+92.3 (c=0.96, CHCl3); 1H NMR (CDCl3).δ1.392 (s, 9H), 2.207 (d, J=7.3 Hz, SH), 3.698 (s, 3H), 4.471 (dd, J=6.7, 6.3 Hz, 1H, CH--S), 4.800 (dd, J=8.7, 6.3 Hz, 1H, CH--N), 5.059 (bd, J=8.7 Hz, 1H, NH), 7.370-7.282 (m, 5H); 13C NMR (CDCl3).δ28.0, 52.1, 59.5, 80.1, 127.5, 127.6, 128.8, 138.8, 155.9, 171.5; IR (KBr) 3335, 2990, 1740, 1685, 1530, 1165 cm-1 ; MS m/z 312 [M+H]+ ;. Anal. Calcd. for C15H21O4NS: C, 57.88; H, 6.75. Found: C, 58.08; H, 6.88.

Workup

  1. customThe volatiles were removed in vacuo
  2. extractionthe residue was extracted with Cl2CH2 (3×)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by flash column chromatography (silica, 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-996c50ee94a049d0b456c23cdc8d06bf
Source dataset
uspto-grants-1997_07
Patent number
US05643872

Reaction notes

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