Potassium Hydroxide → Oxazoline

HRID 1919313Notes

Reaction equation

HRID 1919313 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH3:7])=O)#[C-].FC1C=CC([CH:13]=[O:14])=CC=1.[OH-].[K+].[K].CC1CC[NH:24]CC1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CO.ClCCl>[O:6]1[CH2:4][CH2:3][N:1]=[C:7]1[C:13]([NH2:24])=[O:14].[O:6]1[CH2:4][CH2:3][N:1]=[CH:7]1

Participants

10

Reactant 6

HCID 14797Potassium HydroxideHCID 680234-FluorobenzaldehydeHCID 693814-MethylpiperidineHCID 547815Methyl isocyanoacetateHCID 5462222Potassium2×HCID 18410139Edci hobt

Product 2

HCID 68157OxazolineHCID 22575031Oxazoline amide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 10 (Reaction Scheme 4) was obtained in three synthetic steps. Methyl 2-isocyanoacetate reacted with 4-fluorobenzaldehyde and KOH in MeOH for 7 h at room temperature to afford diastereoselectivity and quantitatively the crude potassium salt trans-ANP 20162. Potassium salt ANP 20162 was coupled with 4-methylpiperidine using the EDCI-HOBT method in dichloromethane to produce the oxazoline amide, LPO 26074 Oxazoline LPO 26074 then underwent ring opening using a HCl 37% solution in MeOH at 45° C. for 15 min to give Compound 10 in 7% yield after purification.

Workup

  1. customto afford diastereoselectivity

Sources & evidence

ORD record
ord-3c09a4313d91486682cedb1c0d5f0e64
Source dataset
uspto-grants-2012_05
Patent number
US08168631B2

Reaction notes

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