Chloroacetonitrile → HCID 72700537, compound

HRID 2208647Notes

Reaction equation

HRID 2208647 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][S:15][S:16][CH3:17])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:19][C:20]#[N:21].C(NC(C)C)(C)C>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][S:15][S:16][CH3:17])[C:10]([O:12][CH2:19][C:20]#[N:21])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7856Chloroacetonitrile2×HCID 7912DiisopropylamineHCID 72700536HCID 72700536, compound

Product 1

HCID 72700537HCID 72700537, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boc-L-Hcm-OH (43 mg, 153 μmol) was dissolved in THF (1 mL). To the solution were added chloroacetonitrile (484 μL, 7.65 mmol) and diisopropylamine (53 μL, 306 μmol). The mixture was stirred overnight under N2 atmosphere. After 18 h, additional chloroacetonitrile (484 L, 7.65 mmol) was added. Concentration under reduced pressure followed by flash chromatography over silica gel with AcOEt-Hexane (3:1) gave the titled compound in (31.3 mg, 63% yield): 1H NMR (360 MHz, CDCl3) δ 5.02 (s, 1H), 4.73 (dd, J=31.3 Hz, 2H) 4.49 (s, 1H), 2.77-2.73 (m, 2H), 2.37 (m, 3H), 2.37-2.27 (m, 1H), 2.13-2.02 (m, 1H), 1.46 (s, 9H); LRMS (ESI) m/z calcd for C12H21N2O4S2 (M+H)+ 321.1. found 321.0.

Workup

  1. waitAfter 18 h
  2. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-5fe78e1342ce4e38b29d76a6e47fc879
Source dataset
uspto-grants-2016_06
Patent number
US09376700B2

Reaction notes

Loading…