Methanol → HCID 58431437, compound

HRID 2095614Notes

Reaction equation

HRID 2095614 reaction equation
C1C2C(COC(=O)N[C@H](C([N:25]3[C:29]4=[N:30][CH:31]=[C:32]([Br:34])[CH:33]=[C:28]4[C:27]([C@H:35]([C:37]4[C:42]([Cl:43])=[CH:41][CH:40]=[C:39]([F:44])[C:38]=4[Cl:45])[CH3:36])=[CH:26]3)=O)CC(C)C)C3C(=CC=CC=3)C=2C=CC=1.CO.C(Cl)Cl>C(#N)C.O>[Br:34][C:32]1[CH:33]=[C:28]2[C:27]([C@H:35]([C:37]3[C:42]([Cl:43])=[CH:41][CH:40]=[C:39]([F:44])[C:38]=3[Cl:45])[CH3:36])=[CH:26][NH:25][C:29]2=[N:30][CH:31]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 58431444HCID 58431444, compound

Product 1

HCID 58431437HCID 58431437, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The procedure described above for the (S)enantiomer was followed, starting with ((S)-1-{5-Bromo-3-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethyl]pyrrolo[2,3-b]pyridine-1-carbonyl}-3-methylbutyl)-carbamic acid 9H-fluoren-9-ylmethyl ester. 1H NMR and LCMS data match with the data for the racemic compound. Optical rotation: [α]25D=+115.7° (c=1.0, MeOH); [α]25D=+151.7° (c=1.0, CH2Cl2). HPLC (Chiralcel OD-RH, solvent 60:40 acetonitrile/water isocratic, flow rate 0.5 mL/min, column temperature 30° C., UV detection at 220 nm): tR=32.1 min.

Sources & evidence

ORD record
ord-097a6197d45a4fdaa7bba8c61a2afda3
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

Loading…