Triethylamine → HCID 46193931, compound

HRID 540400Notes

Reaction equation

HRID 540400 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][N:10]1[C:14]([CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:13][NH:12][CH2:11]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.FC(F)(F)C(O)=O.[NH2:49][C@H:50]([CH2:68][C:69]1[CH:74]=[CH:73][C:72]([O:75][CH3:76])=[CH:71][CH:70]=1)[C:51]([N:53]1[CH2:56][C:55]([CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH2:54]1)=[O:52].[OH-].[Na+]>CN(C=O)C.CCCCCCC>[CH3:76][O:75][C:72]1[CH:71]=[CH:70][C:69]([CH2:68][C@@H:50]([NH:49][C:17](=[O:19])[CH2:16][CH2:15][C:14]2[N:10]([CH3:9])[CH:11]=[N:12][CH:13]=2)[C:51](=[O:52])[N:53]2[CH2:56][C:55]([CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])([C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)[CH2:54]2)=[CH:74][CH:73]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66988493HCID 66988493, compoundHCID 66989200HCID 66989200, compound

Product 1

HCID 46193931HCID 46193931, compoundYield 12.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8900HeptaneSolvent

Procedure

0.17 ml (1.23 mmol) of triethylamine is carefully added to a solution containing 87 mg (0.45 mmol) of 3-(3-methyl-1H-imidazol-4-yl)propionic acid hydrochloride and 160 mg (0.49 mmol) of TBTU in 1 ml of DMF. After stirring for 60 minutes at ambient temperature, 200 mg (0.32 mmol) of (R)-2-amino-3-(4-methoxyphenyl)-1-(3-pentyl-3-phenylazetidin-1-yl)propan-1-one trifluoroacetate (cf. procedure 9-3) are added and the reaction medium is left to stir for three days. The reaction medium is treated with a 2 heptane/8 EtOAc mixture and a 1N aqueous solution of sodium hydroxide. The organic phase is dried over MgSO4, filtered and evaporated. The residue obtained is purified by silica chromatography (eluent 9 DCM/1 MeOH). 21 mg of N—[(R)-1-(4-methoxybenzyl)-2-oxo-2-(3-pentyl-3-phenylazetidin-1-yl)ethyl]-3-(3-methyl-3H-imidazol-4-yl)propionamide are obtained with a yield of 9%.

Workup

  1. waitthe reaction medium is left
  2. stirringto stir for three days
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by silica chromatography (eluent 9 DCM/1 MeOH)

Sources & evidence

ORD record
ord-85edc46ef40a4a519706e95bc325cc82
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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