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Triethylamine → (1R,2R)-2-(4-Chlorophenyl)-N-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-methyloxazole-5-carboxamide

HRID 1419701
Notes
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Reaction equation

HRID 1419701 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=O)=[CH:4][CH:3]=1.C(Cl)(=O)[C:17](Cl)=[O:18].[NH2:22][C@H:23]([CH3:40])[C@:24]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[F:39])([OH:31])[CH2:25][N:26]1[CH:30]=[N:29][CH:28]=[N:27]1.C(N(CC)CC)C>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[O:13][C:11]([C:17]([NH:22][C@H:23]([CH3:40])[C@:24]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=3[F:39])([OH:31])[CH2:25][N:26]3[CH:30]=[N:29][CH:28]=[N:27]3)=[O:18])=[C:9]([CH3:10])[N:8]=2)=[CH:14][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1241470(2S)-2-[(4-chlorophenyl)formamido]propanoic acidHCID 10967497(2R,3R)-3-Amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Product 1

HCID 5480567(1R,2R)-2-(4-Chlorophenyl)-N-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-methyloxazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-(4-chlorobenzoyl)-L-alanine (1.46 g, 6.41 mmol) in benzene (35 mL) was treated with oxalyl chloride (0.55 mL, 6.41 mmol) at 45° C. for 3 h. Next, a solution of (2R,3R)-3-amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1.72 g, 6.41 mmol) and triethylamine (2.2 mL) in CHCl2 (20 mL) was slowly added and the reaction mixture was stirred at 0° C. for 0.5 h. The crude product was then poured into cold water and extracted with CHCl3. The organic solution was dried over Na2SO4, filtered and the filtrate was concentrated in vacuo to give a mixture of several products (TLC) from which the title compound was isolated by flash chromatography as a white solid (140 mg): mp 89°-93° C.; 1H NMR (300 MHz, CDCl3) δ (TMS) 8.04 (d, J=8.5, 2H, arom), 7.79 (s, 1H, triazole), 7.78 (s, 1H, triazole), 7.49 (d, J=8.5, 2H, arom), 7.37 (dt, Jd =6.5, Jt =8.8, 1H, arom), 6.8-6.6 (m, 3H, arom, NH), 5.38 (d, J=1.1, 1H, OH), 5.04 (d, J=14.3, 1H, TrCH(H)), 4.96 (br quint, J=7, 1H, CHMe), 4.53 (d, J=14.3, 1H, TrCH(H)), 2.60 (s, 3H, Me-oxazole), 1.04 (d, J=6.8, 3H, MeCH); HPLC-MS 263 and 265 (ethylaminoacyl group, C13H12ClN2O2), 220 and 222 (acyl group, C11H7ClNO2), 224 (Tr--CH2COHAr, C10H8F2N3O); [α]D =-141° (c 0.5, CHCl3). Analysis calculated for C23H20ClF2N5O3 : C 56.62; H 4.13; N 14.35. Found: C 56.41; H 4.19; N 14.50.

Workup

  1. extractionextracted with CHCl3
  2. dry with materialThe organic solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto give

Sources & evidence

ORD record
ord-4b315e11eb6247d8b18657df3d59e545
Source dataset
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05888941

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes