4-Nitrophenyl chloroformate → HCID 52919311, compound

HRID 515309Notes

Reaction equation

HRID 515309 reaction equation
[NH2:1][C:2]1[C:31]([F:32])=[CH:30][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)=[C:4]([F:33])[CH:3]=1.[C:34](Cl)(=O)[O:35]C1C=CC([N+]([O-])=O)=CC=1.[NH2:47][CH2:48][C:49]([CH3:52])([OH:51])[CH3:50]>O1CCCC1>[F:32][C:31]1[CH:30]=[C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:26])[F:27])[C:21]([F:22])([F:23])[F:24])=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[C:4]([F:33])=[CH:3][C:2]=1[NH:1][C:34]([NH:47][CH2:48][C:49]([OH:51])([CH3:52])[CH3:50])=[O:35]

Participants

5

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 951022-Propanol, 1-amino-2-methyl-HCID 86670953HCID 86670953, compound

Product 1

HCID 52919311HCID 52919311, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-((4-(4-amino-2,5-difluorobenzyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.311 mmol, 150 mg) and 4-nitrophenyl carbonochloridate (0.311 mmol, 62.7 mg) in tetrahydrofuran (5 mL) was stirred at room temperature for 30 minutes. 1-Amino-2-methylpropan-2-ol (0.622 mmol, 0.079 mL, 55.4 mg) was added and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the residue purified by column chromatography (eluent: 2-10% methanol in dichloromethane) to afford the title compound (89.5 mg). MS (ESI) m/z 598.2 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue purified by column chromatography (eluent: 2-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-d6152d84965d4ed99bf0bb221e2e3f37
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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