Hexane → HCID 57261056, compound
Reaction equation
C([S:4][CH2:5][C@@H:6]([C:19]([F:22])([F:21])[F:20])[C:7]([NH:9][C@@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C:12]([OH:14])=[O:13])=[O:8])(=O)C.[OH-].[NH4+].CCCCCC.C(OCC)(=O)C>O.CO.C(O)(=O)C>[F:20][C:19]([F:21])([F:22])[C@H:6]([CH2:5][SH:4])[C:7]([NH:9][C@@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C:12]([OH:14])=[O:13])=[O:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
A suspension of the (S,R) isomer product of Example 35 (1.0 g., 2.9 mmol.) in water maintained at 0° C. under argon was treated with ammonium hydroxide (5M solution, 10 mL, 50 mmol.) and stirred for 5 minutes. The reaction was quenched at 0° C. with 140 mL of 10% potassium bisulfate and then extracted with ethyl acetate (4×). The organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo to yield 1.0 g. of yellow solid. The crude reaction product was flash chromatographed on 200 mL of silica gel eluting with hexane:ethyl acetate (2:1) to isolate 0.61 g. of the title (S,R) isomer product as a white solid, m.p. 155°-156° C., TLC Rf =0.19 (hexane:ethyl acetate:acetic acid, 100:100:1). [α]D =-55.5° (c=0.89, methanol).
Workup
- customThe reaction was quenched at 0° C. with 140 mL of 10% potassium bisulfate
- extractionextracted with ethyl acetate (4×)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto yield 1.0 g
- customThe crude reaction product
- customchromatographed on 200 mL of silica gel eluting with hexane:ethyl acetate (2:1)
- customto isolate 0.61 g
Sources & evidence
- ORD record
- ord-760d7ac0e07742d09f720a98a90b26d5
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05223516
Reaction notes
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