Hydrochloric Acid → N-[(1,1-Dimethylethoxy)carbonyl]-3-(methyldithio)-L-alanine

HRID 2208644노트

반응식

HRID 2208644 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][SH:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][S-:16].[Na+].II.Cl>O.C1COCC1.CCO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][S:14][S:16][CH3:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 152319N-tert-ButyloxycarbonylcysteineHCID 4378561Sodium methanethiolate

생성물 1

HCID 14402896N-[(1,1-Dimethylethoxy)carbonyl]-3-(methyldithio)-L-alanine수율 68%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

(R)-2-((tert-butoxycarbonyl)amino)-3-mercaptopropanoic acid (Boc-L-Cys-OH) (110 mg, 0.5 mmol) was dissolved in H2O/THF (50% v/v, 20 mL). To the solution was added sodium thiomethoxide (350 mg, 5.0 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 5.5 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 in EtOAc/Hexanes/AcOH (75:25:1) gave Boc-L-Csm-OH (90.8 mg, 68% yield). 1H NMR (360 MHz, CDCl3) δ 5.34 (s, 1H), 4.63 (br, s, 1H), 3.26-3.16 (m, 2H), 2.43 (m, 3H), 1.47 (s, 9H); LRMS (ESI) m/z calcd for C9H18NO4S2 (M+H)+ 268.1. found 268.2.

후처리

  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

출처 및 근거

ORD 기록
ord-3b9ae90225ef4508839197662031c20e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376700B2

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