Sodium Bicarbonate → HCID 86609475, compound

HRID 1171731Notes

Reaction equation

HRID 1171731 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([N:14]1[CH2:19][CH2:18][C@@H:17]([SH:20])/[C:16](=[CH:21]/[C:22]2[CH:26]=[CH:25][N:24]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:23]=2)/[CH2:15]1)[C:10]([O:12][CH3:13])=[O:11].C(=O)([O-])O.[Na+]>CC(O)C.CCCCCC>[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C@H:9]([N:14]1[CH2:19][CH2:18][C@@H:17]([SH:20])/[C:16](=[CH:21]/[C:22]2[CH:26]=[CH:25][N:24]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:23]=2)/[CH2:15]1)[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86609472HCID 86609472, compound

Product 1

HCID 86609475HCID 86609475, compound

Reagents, catalysts & solvents 1

HCID 21585144Isopropanol hexaneSolvent

Procedure

(4R)-(E)-1-[(1RS)-1-(2-Fluorophenyl)-2-methoxy-2-oxoethyl]-3-({1-[2-(ethoxycarbonyl)ethyl]-1H-pyrazol-3-yl}methylidene)-4-sulfanylpiperidine hydrochloride was treated with an aqueous sodium hydrogen carbonate solution. The liberated base was extracted with dichloromethane. The free base thus obtained (ca. 200 mg) was divided into five portions and subjected to preparative HPLC (Chiralcel OD-H, 20φ×250 mm, Daicel Chemical Industries Co., Ltd., eluent: 2-propanol/hexane=1/2, 4 ml/minute) to afford the more mobile isomer, (4R)-(E)-1-[(1S)-1-(2-fluorophenyl)-2-methoxy-2-oxoethyl]-3-({1-[2-(ethoxycarbonyl)ethyl]-1H-pyrazol-3-yl}methylidene)-4-sulfanylpiperidine (103.9 mg), and the less mobile isomer, (4R)-(E)-1-[(1R)-1-(2-fluorophenyl)-2-methoxy-2-oxoethyl]-3-({1-[2-(ethoxycarbonyl)ethyl]-1H-pyrazol-3-yl}methylidene)-4-sulfanylpiperidine (100.3 mg), both as colourless oils.

Workup

  1. extractionThe liberated base was extracted with dichloromethane
  2. customThe free base thus obtained (ca. 200 mg)

Sources & evidence

ORD record
ord-4622cd9b9b8f4ff385c2a75e1f5660a7
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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