(S)-2-amino-1-(3-chlorophenyl)ethanol → HCID 69425530, compound

HRID 970359Notes

Reaction equation

HRID 970359 reaction equation
C(OC(=O)C(NCC(C1C=CC=C(Cl)C=1)O)=C(C1N(C(OC(C)(C)C)=O)C2C=C(N3CCOCC3)C=C(C)C=2N=1)C(OCC)=O)C.[CH2:47]([O:49][C:50](=[O:86])[C:51]([O:81]S(C)(=O)=O)=[C:52]([C:58]1[N:62]([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[C:61]2[CH:70]=[C:71]([N:75]3[CH2:80][CH2:79][O:78][CH2:77][CH2:76]3)[CH:72]=[C:73]([CH3:74])[C:60]=2[N:59]=1)[C:53]([O:55][CH2:56][CH3:57])=[O:54])[CH3:48].NC[C@H](C1C=CC=C(Cl)C=1)O>C(#N)C>[CH2:56]([O:55][C:53](=[O:54])[CH:52]([C:58]1[N:62]([C:63]([O:65][C:66]([CH3:67])([CH3:69])[CH3:68])=[O:64])[C:61]2[CH:70]=[C:71]([N:75]3[CH2:76][CH2:77][O:78][CH2:79][CH2:80]3)[CH:72]=[C:73]([CH3:74])[C:60]=2[N:59]=1)[C:51](=[O:81])[C:50]([O:49][CH2:47][CH3:48])=[O:86])[CH3:57]

Participants

5

Reactant 3

HCID 9855591(S)-2-amino-1-(3-chlorophenyl)ethanolHCID 72491576HCID 72491576, compoundHCID 72491578HCID 72491578, compound

Product 1

HCID 69425530HCID 69425530, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

(S)-(2E and 2Z)-2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-but-2-enedioic acid diethyl ester: To a stirred solution of (2-E and 2Z)-2-methanesulfonyloxy-3-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-but-2-enedioic acid diethyl ester (0.012 g, 0.021 mmol) in acetonitrile (1 mL) was added (S)-2-amino-1-[3-chlorophenyl]ethanol (0.005 g, 0.031 mmol) and the mixture was stirred at 60° C. for 1 hour. The solvent was evaporated and the residue was purified by silica gel chromatography (50 to 75% ethyl acetate in hexane) to give the title material (0.010 g, 74%). HPLC: 97% (220 nm), LCMS (+ESI, M+H+) m/z 657; 1H NMR (400 MHz, acetone-d6) δ (ppm): 1.17-1.33 (15H, m), 2.51 (3H, br s), 3.14 (4H, m), 3.77 (6H, m), 4.24-4.34 (4H, m), 5.62 (1H, m), 6.80-7.52 (6H, m).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel chromatography (50 to 75% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1fd157300e06405ba32e304ea14b2a4d
Source dataset
uspto-grants-2007_12
Patent number
US07312215B2

Reaction notes

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