Triethylamine → (2R)-2-{[6-(methyloxy)-3-nitro-2-pyridinyl]amino}-3-[(phenylmethyl)oxy]-1-propanol

HRID 420684Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4].CCN(CC)CC.Cl[C:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[C:24]([O:31][CH3:32])[N:23]=1>CCO>[CH3:32][O:31][C:24]1[N:23]=[C:22]([NH:1][C@@H:2]([CH2:5][O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3][OH:4])[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 78 °C

Procedure

To a solution of (R)-2-amino-3-benzyloxy-1-propanol (698.4 g, 3.931 mol) in EtOH (3.6 L) was added Et3N (1.27 L, 9.11 mol) in portions over 10 min. Then a solution of 2-chloro-6-methoxy-3-nitropyridine (672.7 g, 3.567 mol) in EtOH (0.6 L) was added in portions over 10 min. The mixture was heated at 78° C. for 2 h. The reaction mixture was cooled to room temperature and added to stirred ice/H2O (8.4 L). The mixture was extracted with EtOAc (9+6+3 L). The extracts were washed with brine (6 L), dried over MgSO4 (˜900 g), filtered and evaporated to give (2R)-2-{[6-(methyloxy)-3-nitro-2-pyridinyl]amino}-3-[(phenylmethyl)oxy]-1-propanol (1373.1 g, 115%) as an orange oil.

Workup

temperatureThe reaction mixture was cooled to room temperature
additionadded
extractionThe mixture was extracted with EtOAc (9+6+3 L)
washThe extracts were washed with brine (6 L)
dry with materialdried over MgSO4 (˜900 g)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-f8553a3ce95e4c90acce6d9c2c9de537
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097628B2

Reaction notes

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