Toluene → HCID 10257257, compound

HRID 441195Notes

Reaction equation

HRID 441195 reaction equation
Cl.C[N:3](C)CCCN=C=NCC.ClC(Cl)[C:15]([OH:17])=[O:16].C(OC([C:29]1[C:30](=[O:58])[N:31]([CH2:44][C:45]([NH:47][CH:48]([CH:55]([CH3:57])[CH3:56])[CH:49]([OH:54])[C:50]([F:53])([F:52])[F:51])=[O:46])[CH:32]=[C:33]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=2)[C:34]=1N)=O)C1C=CC=CC=1.[C:59]1([CH3:65])[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1>CS(C)=O>[CH2:65]([O:17][C:15]([NH:3][C:29]1[C:30](=[O:58])[N:31]([CH2:44][C:45]([NH:47][CH:48]([CH:55]([CH3:57])[CH3:56])[C:49](=[O:54])[C:50]([F:53])([F:52])[F:51])=[O:46])[CH:32]=[C:33]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=2)[CH:34]=1)=[O:16])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6597Dichloroacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22405453HCID 22405453, compound

Product 1

HCID 10257257HCID 10257257, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.51 g) in dimethyl sulfoxide (2 mL), toluene (4 mL) and dichloroacetic acid (0.14 g) was added 2-[3-benzyloxycarbonyl-amino-5-(3-fluorobenzyl)-2-oxo-1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (0.15 g). The mixture was allowed to stir overnight and was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organics were washed (brine), dried, evaporated, and purified using chromatography, with dichloromethane as the eluent to yield the title compound (80%); NMR: 0.79-0.97 (m,6), 2.21 (m,1), 4.06 (m, NHCH hydrate), 4.49-4.81 (m,3, NHCH keto, CH2CO), 5.13 (s,2, CH2), 6.95 (m, OH hydrate), 7.01-7.07 (m,3, phenyl), 7.22-7.40 (m,7, phenyl), 7.72 (m,1, pyridone), 7.82 (d,J=10.5, NH hydrate), 8.36 (s, NH hydrate), 8.40 (s, NH keto), 8.92 (d,J=6.5, NH keto form).

Workup

  1. customwas partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. washThe organics were washed (brine)
  3. customdried
  4. customevaporated
  5. custompurified

Sources & evidence

ORD record
ord-c5e4b582d03540c18e0f836c1103baf6
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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