Triethylamine → HCID 178450006, compound

HRID 540434Notes

Reaction equation

HRID 540434 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.Cl.[CH2:31]([C:38]([OH:40])=O)[CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1.[NH2:41][C@H:42]([CH2:61][C:62]1[CH:67]=[CH:66][C:65]([O:68][CH3:69])=[CH:64][CH:63]=1)[C:43]([N:45]1[CH2:48][C:47]([O:56][CH2:57][C:58]#[C:59][CH3:60])([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[CH3:55])[CH2:46]1)=[O:44].[OH-].[Na+]>CN(C)C=O>[CH2:57]([O:56][C:47]1([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[CH3:55])[CH2:48][N:45]([C:43](=[O:44])[C@H:42]([NH:41][C:38](=[O:40])[CH2:31][CH2:32][C:33]2[N:37]=[CH:36][NH:35][CH:34]=2)[CH2:61][C:62]2[CH:67]=[CH:66][C:65]([O:68][CH3:69])=[CH:64][CH:63]=2)[CH2:46]1)[C:58]#[C:59][CH3:60]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66988366(R)-2-amino-1-(3-but-2-ynyloxy-3-o-tolyl-azetidin-1-yl)-3-(4-methoxyphenyl)propan-1-oneHCID 178479756HCID 178479756, compound

Product 1

HCID 178450006HCID 178450006, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

732 mg (2.3 mmol) of TBTU and 1 ml (7 mmol) of triethylamine are added to a solution of 408 mg (2.3 mmol) of desamino-histidine hydrochloride in 6 ml of dimethylformamide. After stirring for 10 min, 751 mg (1.8 mmol) of (R)-2-amino-1-(3-but-2-ynyloxy-3-o-tolyl-azetidin-1-yl)-3-(4-methoxyphenyl)propan-1-one in 6 ml of dimethylformamide are added. The reaction medium is stirred for 115 hours at ambient temperature and then a 1N aqueous solution of sodium hydroxide is added and the medium is extracted with a 1/1 heptane/ethyl acetate mixture. The organic phase is dried over sodium sulphate, filtered and concentrated. The residue obtained is purified by silica gel chromatography, elution being carried out with a 90/10 dichloro-methane/methanol mixture. 362 mg of N—[(R)-2-(3-but-2-ynyloxy-3-o-tolylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]-3-(1H-imidazol-4-yl)propionamide are obtained in the form of a white solid with a yield of 40%.

Workup

  1. stirringThe reaction medium is stirred for 115 hours at ambient temperature
  2. extractionthe medium is extracted with a 1/1 heptane/ethyl acetate mixture
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customis purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-8424645a68174800926a2910cc98fd8f
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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