Acetonitrile → (3R)-3-acetamido-3-phenylpropanoic acid

HRID 1158370Notes

Reaction equation

HRID 1158370 reaction equation
[C:1]([NH:4][C:5]1([CH2:10][C:11]([OH:13])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].N[C@@H:15](C1C=CC=CC=1)[CH2:16]C(O)=O.CC#N.O.CC#N>O>[C:1]([NH:4][C@@H:5]([C:9]1[CH:8]=[CH:7][CH:6]=[CH:16][CH:15]=1)[CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 686703(3R)-3-amino-3-phenylpropanoic acidHCID 18373917Acetonitrile--water (1/1)2×HCID 451192642-(1-Acetamidocyclopentyl)acetic acid

Product 1

HCID 746298(3R)-3-acetamido-3-phenylpropanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound is prepared analogously as described for (1-acetylamino-cyclopentyl)-acetic acid from (R)-3-amino-3-phenylpropionic acid. MS (LC-MS): [M+H]+=208.2. tR (HPLC, Waters Symmetry C18 column, 10-95% CH3CN/H2O/3.5 min, 95% CH3CN/H2O, 2 min, CH3CN and H2O containing 0.1% TFA, flow: 0.6 mL/min): 1.16 min.

Workup

  1. custom1.16 min.

Sources & evidence

ORD record
ord-fbe8eeb9931246d28a812386c40c8c0f
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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