Hydrochloric Acid → HCID 22798347, compound

HRID 2208645Notes

Reaction equation

HRID 2208645 reaction equation
[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[OH-].[Na+].[CH3:17][CH:18]([SH:20])[CH3:19].II.Cl>O.C1COCC1.CCO>[C:11]([O:10][C:8]([NH:1][C@@H:2]([CH2:3][S:4][S:20][CH:18]([CH3:19])[CH3:17])[C:5]([OH:7])=[O:6])=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 63642-PropanethiolHCID 14798Sodium HydroxideHCID 152319N-tert-Butyloxycarbonylcysteine

Product 1

HCID 22798347HCID 22798347, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Boc-L-Cys-OH (221 mg, 1.0 mmol) was dissolved in H2O/THF (50% v/v, 20 mL). To the solution was added 10 N sodium hydroxide aq. (1.2 mL, 12 mmol) and 2-propane thiol (929 uL, 10 mmol) at 0° C. Then, a solution of iodine in 95% EtOH was added dropwise until the color of the reaction system changed from colorless to brown. The mixture was stirred for 1 d with warming to room temperature. After removing THF under reduced pressure, reaction mixture was neutralized by 1 N HCl aq. until pH 2-3. The solution was extracted with EtOAc. The extract was washed with saturated aq. NaS2O4 and brine, and dried over MgSO4. Concentration under reduced pressure followed by flash chromatography over silica gel in EtOAc/Hexanes/AcOH (75:25:1) gave Boc-L-Csp-OH (145.7 mg, 49% yield): 1H NMR (360 MHz, CDCl3) δ 5.34 (s, 1H), 4.59 (br, s, 1H), 3.24-3.14 (m, 2H), 3.09-3.00 (m, 1H), 1.47 (s, 9H), 1.32-1.30 (dd, 6H); LRMS (ESI) m/z calcd for C11H22NO4S2 (M+H)+ 296.1. found 296.1.

Workup

  1. customAfter removing THF
  2. customunder reduced pressure, reaction mixture
  3. extractionThe solution was extracted with EtOAc
  4. washThe extract was washed with saturated aq. NaS2O4 and brine
  5. dry with materialdried over MgSO4
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-de012e366fe446708e931e2e5a737db1
Source dataset
uspto-grants-2016_06
Patent number
US09376700B2

Reaction notes

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