HCID 49833869, compound → HCID 49833692, compound

HRID 473846Notes

Reaction equation

HRID 473846 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]4[O:20][CH2:19][CH2:18][N:17]([C:21]([N:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]5[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[O:22])[CH2:16][C:15]=4[CH:35]=3)[CH:9]=[CH:10][C:4]=2[N:3]=1>C(O)C.CO>[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]4[O:20][CH2:19][CH2:18][N:17]([C:21]([N:23]5[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]5[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[O:22])[CH2:16][C:15]=4[CH:35]=3)[CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 49833869HCID 49833869, compound

Product 1

HCID 49833692HCID 49833692, compound

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent2×

Procedure

Prepared by chiral preparative HPLC separation of racemic 7-(2-methyl-1H-benzimidazol-6-yl)-4-[(2-phenylpiperidin-1-yl)carbonyl]-2,3,4,5-tetrahydro-1,4-benzoxazepine (example 1) using a SHIMADZU LC-20AD apparatus equipped with a Chiralpak AD-H, 25 cm×4.6 mm column using a mobile phase of ethanol:methanol 1:1 and flow rate of 18.0 mL/min and detection at 220 nm. The isomer with retention time 11.20 min. was assigned as the (R)-enantiomer. Chiral analytical HPLC was carried out using a SHIMADZU LC-20AD apparatus equipped with a Chiralpak AD-H, 25 cm×4.6 mm column using a mobile phase of ethanol:methanol 1:1 and flow rate of 0.7 mL/min with detection at 254/220 nm. This isomer gave a retention time 9.51 min and ee>99%. MS (EI) C29H30N4O2: 467 (MH+).

Workup

  1. customequipped with a Chiralpak AD-H, 25 cm×4.6 mm column
  2. customequipped with a Chiralpak AD-H, 25 cm×4.6 mm column
  3. customThis isomer gave a retention time 9.51 min and ee>99%

Sources & evidence

ORD record
ord-57957190658e4b5c97ba802612a654eb
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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