2,6-Lutidine → phenylmethyl 2-{(1S)-3-iodo-1-[(methyloxy)carbonyl]propyl}hydrazinecarboxylate

HRID 1396835Notes

Reaction equation

HRID 1396835 reaction equation
O[C@H:2]([CH2:7][CH2:8][I:9])[C:3]([O:5][CH3:6])=[O:4].N1C(C)=CC=CC=1C.[NH:18]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[NH2:19]>C(Cl)Cl>[I:9][CH2:8][CH2:7][C@H:2]([NH:19][NH:18][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 79242Benzyl carbazateHCID 54371593methyl (2R)-2-hydroxy-4-iodobutanoate

Product 1

HCID 68287973phenylmethyl 2-{(1S)-3-iodo-1-[(methyloxy)carbonyl]propyl}hydrazinecarboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (2R)-2-hydroxy-4-iodobutanoate (3.35 g, 13.7 mmol) in DCM (100 mL) under N2 at −70° C. was added 2,6-lutidine (5.67 g, 55 mmol), followed by triflate anhydride (4.07 g, 144.4 mmol) dropwise. Stirring continued at the same temperature for 1 hour. Phenylmethyl hydrazinecarboxylate (2.74 g, 16.5 mmol) was added in one portion, and the reaction mixture was allowed to warm up to room temperature and stirred for 24 hours. The reaction mixture was concentrated, and the crude oil was purified by column chromatography (PE:EA=20:1 to 1:1) to provide phenylmethyl 2-{(1S)-3-iodo-1-[(methyloxy)carbonyl]propyl}hydrazinecarboxylate as yellow oil (3.7 g, 83%). 1H NMR (300 MHz, CDCl3) δ 7.35-7.34 (m, 5H), 6.51 (s, 1H), 5.13 (s, 2H), 4.27 (s, 1H), 3.76-3.70 (m, 4H), 3.42-3.30 (m, 2H), 2.25-2.06 (m, 2H).

Workup

  1. stirringstirred for 24 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude oil was purified by column chromatography (PE:EA=20:1 to 1:1)

Sources & evidence

ORD record
ord-306a7297c5e94586a6fc8811d3a8f724
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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