Ethanol → HCID 178481914, compound

HRID 516455Notes

Reaction equation

HRID 516455 reaction equation
[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.CN(C(ON1N=NC2C=CC(=CC1=2)Cl)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C([O:47][C:48](=[O:68])[C@H:49]([OH:67])[CH2:50][C@H:51]([NH2:66])[CH2:52][C:53]1[CH:58]=[CH:57][C:56]([C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([Cl:65])[CH:60]=2)=[CH:55][CH:54]=1)C.CCO.[Li+].[OH-].O>CN(C=O)C>[Cl:65][C:61]1[CH:60]=[C:59]([C:56]2[CH:55]=[CH:54][C:53]([CH2:52][C@@H:51]([NH:66][C:8]([C:4]3[CH:3]=[C:2]([OH:1])[N:6]([CH3:7])[N:5]=3)=[O:10])[CH2:50][C@@H:49]([OH:67])[C:48]([OH:68])=[O:47])=[CH:58][CH:57]=2)[CH:64]=[CH:63][CH:62]=1

Participants

9

Reactant 7

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 81531DiisopropylethylamineHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphateHCID 86682253(2R,4R)-4-amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl esterHCID 178481916HCID 178481916, compound

Product 1

HCID 178481914HCID 178481914, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Hydroxy-1-methyl-1H-pyrazole-3-carboxylic acid (19.6 mg, 138 μmol) was combined with HCTU (56.9 mg, 138 μmol) in DMF. The mixture was stirred for 10 minutes at room temperature before adding DIPEA (72 μL, 413 μmol) and (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (50 mg, 0.1 mmol). The resulting mixture was stirred overnight at room temperature. EtOH (402 μL, 6.9 mmol) and 1 M LiOH in water (1.1 mL, 1.1 mmol) was added and the mixture was stirred at room temperature for 1 hour. The mixture was evaporated under reduced pressure and purified by preparative HPLC to yield the title compound (6.4 mg). MS m/z [M+H]+ calc'd for C22H22ClN3O5, 444.12. found 444.4.

Workup

  1. stirringThe resulting mixture was stirred overnight at room temperature
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. customThe mixture was evaporated under reduced pressure
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-98d8baac5d6e4b2896a34a4c3ad1f125
Source dataset
uspto-grants-2015_08
Patent number
US09108934B2

Reaction notes

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