Sodium Hydroxide → 1-(4-(3-(Cyclopropylmethyl)ureido)benzoyl)-4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-2-carboxylic acid

HRID 1807779Notes

Reaction equation

HRID 1807779 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:43])[NH:7][C:8]2[CH:42]=[CH:41][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]([OH:36])([C:32]([F:35])([F:34])[F:33])[C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=4)[CH2:16][CH:15]3[C:37]([O:39]C)=[O:38])=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([CH2:4][NH:5][C:6](=[O:43])[NH:7][C:8]2[CH:42]=[CH:41][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]([OH:36])([C:28]([F:31])([F:30])[F:29])[C:32]([F:34])([F:35])[F:33])=[CH:23][CH:22]=4)[CH2:16][CH:15]3[C:37]([OH:39])=[O:38])=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59175829Methyl 1-(4-(3-(cyclopropylmethyl)ureido)benzoyl)-4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-2-carboxylate

Product 1

HCID 591758861-(4-(3-(Cyclopropylmethyl)ureido)benzoyl)-4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-2-carboxylic acidYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-(4-(3-(cyclopropylmethyl)ureido)benzoyl)-4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-2-carboxylate (0.032 mmol, 0.02 g) and sodium hydroxide (0.032 mmol, 1.298 mg) were combined and heated to 80° C. in methanol (1 mL) for 6 hours in a reactivial. The reaction mixture was concentrated under reduced pressure. The resulting residue was passed down an SCX column to afford the title compound (16 mg). MS (ESI) m/z 603.2 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6e9d1f73ae1a4916bbffd79fbbe3452f
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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