Tetrahydrofuran → HCID 66665531, compound

HRID 2196244Notes

Reaction equation

HRID 2196244 reaction equation
[NH2:1][C@@:2]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([Br:16])[CH:8]=1)([CH3:6])[C:3](O)=[O:4].C1COCC1>C(OCC)(=O)C>[NH2:1][C@@:2]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([Br:16])[CH:8]=1)([CH3:6])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 66665328(R)-2-Amino-2-(3-bromo-5-nitro-phenyl)-propionic acid

Product 1

HCID 66665531HCID 66665531, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-2-Amino-2-(3-bromo-5-nitro-phenyl)-propionic acid (8.41 g, 25.8 mmol) was suspended in abs. THF (39 ml) and cooled to 0° C. BH3 in THF (103 ml, 103 mmol, 1M in THF) was added and the reaction was stirred at r.t. for 1 hr. The reaction was poured onto NaHCO3 (solid, 26 g, 12 eq.), 78 g ice and 155 ml ethyl acetate and stirred for 20 min. at r.t. Phases were separated. The organic phases were washed with water and brine, combined and dried over Na2SO4. Volatiles were removed under reduced pressure yielding the title compound as brown oil. 1H-NMR (360 MHz, DMSO-d6): 8.40 (s, 1H), 8.25 (s, 1H), 8.18 (s, 1H), 4.95 (t, 1H), 3.55 (m, 1H), 3.38 (m, 1H), 1.33 (s, 3H); MS: 275 [(M+H)+].

Workup

  1. stirringstirred for 20 min. at r.t
  2. customPhases were separated
  3. washThe organic phases were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customVolatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-5024548667904109a448d36a4615ee15
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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