Hydrochloric Acid → HCID 72700536, compound

HRID 2208646Notes

Reaction equation

HRID 2208646 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][SH:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][S-:17].[Na+].II.Cl>O.C1COCC1.CCO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][S:15][S:17][CH3:16])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 4378561Sodium methanethiolateHCID 15000978HCID 15000978, compound

Product 1

HCID 72700536HCID 72700536, compoundYield 159.3%

Reagents, catalysts & solvents 2

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

Procedure

(S)-2-((tert-butoxycarbonyl)amino)-4-mercaptobutanoic acid (Boc-L-Hcs-OH) (188 mg, 0.4 mmol) was dissolved in H2O/THF (50% v/v, 16 mL). To the solution was added sodium thiomethoxide (560 mg, 8.0 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 1.5 h 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 NaS2O4 aq. and brine, and dried over MgSO4. Concentration under reduced pressure followed by flash chromatography over silica gel with EtOAc/Hexanes/AcOH (75:25:1) gave Boc-L-Hcm-OH (179.3 mg, 80% yield): 1H NMR (360 MHz, CDCl3) δ 5.06 (s, 1H), 4.44 (s, 1H), 2.78 (t, J=7.7 Hz, 2H), 2.42 (s, 3H), 2.35 (m, 1H), 2.09 (m, 1H), 1.45 (s, 9H); LRMS (ESI) m/z calcd for C10H20NO4S2 (M+H)+ 282.1. found 282.1.

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 NaS2O4 aq. and brine
  5. dry with materialdried over MgSO4
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-6151950de3c44caa894de9c4494b079d
Source dataset
uspto-grants-2016_06
Patent number
US09376700B2

Reaction notes

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