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Sodium Hydroxide → 1-{4'-[5-((R)-1,2-dimethyl-propoxycarbonylamino)-1-methyl-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid

HRID 631919
Notes
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Reaction equation

HRID 631919 reaction equation
C[O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[N:21]=[N:22][N:23]([CH3:34])[C:24]=4[NH:25][C:26]([O:28][C@H:29]([CH3:33])[CH:30]([CH3:32])[CH3:31])=[O:27])=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>C1COCC1.C(O)C>[CH3:33][C@@H:29]([O:28][C:26]([NH:25][C:24]1[N:23]([CH3:34])[N:22]=[N:21][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:10]=[CH:9][C:8]([C:5]3([C:3]([OH:4])=[O:2])[CH2:7][CH2:6]3)=[CH:13][CH:12]=2)=[CH:15][CH:16]=1)=[O:27])[CH:30]([CH3:31])[CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 1180622341-{4'-[5-((R)-1,2-dimethyl-propoxycarbonylamino)-1-methyl-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid methyl ester

Product 1

HCID 714574791-{4'-[5-((R)-1,2-dimethyl-propoxycarbonylamino)-1-methyl-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acidYield 89.3%

Reagents, catalysts & solvents 2

HCID 702Ethanol
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

1-{4′-[5-((R)-1,2-Dimethyl-propoxycarbonylamino)-1-methyl-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid methyl ester (97 mg) was dissolved in 2 mL of THF and 2 mL of ethanol. To this clear solution was added 1N NaOH solution 2 mL. The clear solution was stirred at room temperature overnight. Solvents were evaporated and the residue was dissolved in water (12 mL). The solution was filtered. The filtrate was treated with hydrochloric acid (1N, 2.5 mL). The white precipitate was filtered and dried in air to provide 1-{4′-[5-((R)-1,2-dimethyl-propoxycarbonylamino)-1-methyl-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid as a pale yellow solid (84 mg, 89.3% yield). LC/MS calcd for C25H28N4O4 (m/e) 448.0, obsd 449.2 (M+H); 1H-NMR (300 MHz, DMSO-d6) δ ppm 0.52 (br, 1H), 0.88 (br, 5H), 1.04-1.25 (m, 5H), 1.35-1.43 (m, 2H), 1.62-1.85 (br, 1H), 3.80 (s, 3H), 4.55 (br, 1H), 7.35 (d, J=8.3 Hz, 2H), 7.57 (d, J=8.3 Hz, 2H), 7.68 (d, J=8.3 Hz, 2H), 7.78 (d, J=8.3 Hz, 2H), 9.34 and 9.67 (br s, 1H), 12.30 (br s, 1H).

Workup

  1. customSolvents were evaporated
  2. dissolutionthe residue was dissolved in water (12 mL)
  3. filtrationThe solution was filtered
  4. additionThe filtrate was treated with hydrochloric acid (1N, 2.5 mL)
  5. filtrationThe white precipitate was filtered
  6. customdried in air

Sources & evidence

ORD record
ord-a2fb32dd791543a792590208b1e63589
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321738B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes