Piperidine → 4'-{(R)-1-[(3-Amino-oxetane-3-carbonyl)-amino]-ethyl}-3-chloro-3'-fluoro-biphenyl-2-carboxylic acid methyl ester

HRID 1404546Notes

Reaction equation

HRID 1404546 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([C:12]2[CH:17]=[CH:16][C:15]([C@H:18]([NH:20][C:21]([C:23]3([NH:27]C(OCC4C5C=CC=CC=5C5C4=CC=CC=5)=O)[CH2:26][O:25][CH2:24]3)=[O:22])[CH3:19])=[C:14]([F:45])[CH:13]=2)=[CH:7][CH:8]=[CH:9][C:10]=1[Cl:11])=[O:4].N1CCCCC1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:6]([C:12]2[CH:17]=[CH:16][C:15]([C@H:18]([NH:20][C:21]([C:23]3([NH2:27])[CH2:24][O:25][CH2:26]3)=[O:22])[CH3:19])=[C:14]([F:45])[CH:13]=2)=[CH:7][CH:8]=[CH:9][C:10]=1[Cl:11])=[O:4]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 679793093-Chloro-4'-((R)-1-{[3-(9H-fluoren-9-ylmethoxycarbonylamino)-oxetane-3-carbonyl]-amino}-ethyl)-3'-fluoro-biphenyl-2-carboxylic acid methyl ester

Product 1

HCID 679794974'-{(R)-1-[(3-Amino-oxetane-3-carbonyl)-amino]-ethyl}-3-chloro-3'-fluoro-biphenyl-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chloro-4′-((R)-1-{[3-(9H-fluoren-9-ylmethoxycarbonylamino)-oxetane-3-carbonyl]-amino}-ethyl)-3′-fluoro-biphenyl-2-carboxylic acid methyl ester (100 mg, 159 μmol, step C) in dry DMF (1.8 ml) was added piperidine (0.2 ml) and the solution was stirred at room temperature for 2 h. The brown solution was concentrated to dryness under high vacuum. The remaining residue was purified by chromatography (silica gel; DCM/MeOH 98:2) and the title compound was obtained as white solid (60 mg, 92%). MS: 407.2 [M+H]+.

Workup

  1. concentrationThe brown solution was concentrated to dryness under high vacuum
  2. customThe remaining residue was purified by chromatography (silica gel; DCM/MeOH 98:2)

Sources & evidence

ORD record
ord-f1dc5266dbb94872b3898c60f04ea889
Source dataset
uspto-grants-2014_12
Patent number
US08912221B2

Reaction notes

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