Triethylamine → HCID 178450010, compound

HRID 540418Notes

Reaction equation

HRID 540418 reaction equation
C(N(CC)CC)C.[OH:8][C@@H:9]([CH2:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1)[C:10]([OH:12])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[NH2:42][C@H:43]([CH2:62][C:63]1[CH:68]=[CH:67][C:66]([O:69][CH3:70])=[CH:65][CH:64]=1)[C:44]([N:46]1[CH2:49][C:48]([O:57][CH2:58][CH2:59][CH2:60][CH3:61])([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[CH3:56])[CH2:47]1)=[O:45].[OH-].[Na+]>CN(C)C=O>[CH2:58]([O:57][C:48]1([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[CH3:56])[CH2:49][N:46]([C:44](=[O:45])[C@H:43]([NH:42][C:10](=[O:12])[C@@H:9]([OH:8])[CH2:13][C:14]2[N:15]=[CH:16][NH:17][CH:18]=2)[CH2:62][C:63]2[CH:68]=[CH:67][C:66]([O:69][CH3:70])=[CH:65][CH:64]=2)[CH2:47]1)[CH2:59][CH2:60][CH3:61]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66988286(R)-2-amino-1-(3-butoxy-3-o-tolylazetidin-1-yl)-3-(4-methoxyphenyl)propan-1-one hydrochlorideHCID 178525822HCID 178525822, compound

Product 1

HCID 178450010HCID 178450010, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.1 ml (0.8 mmol) of triethylamine is added to a solution containing 50 mg (0.3 mmol) of (S)-2-hydroxy-3-(1H-imidazol-4-yl)propanoic acid and 100 mg (0.3 mmol) of TBTU in 2 ml of dimethylformamide. After stirring for 1 hour at ambient temperature, 128 mg (0.3 mmol) of (R)-2-amino-1-(3-butoxy-3-o-tolyl-azetidin-1-yl)-3-(4-methoxyphenyl)propan-1-one hydro-chloride (described in Example 6.2) are added and the mixture is stirred for 72 h at ambient temperature. A 1N aqueous solution of sodium hydroxide is added and the medium is extracted with a 20/80 heptane/ethyl acetate mixture. The organic phase is dried over magnesium sulphate, filtered and concentrated. The crude product is purified by preparative thin layer chromatography (eluent: 90/10 dichloro-methane/methanol). 17 mg of (S)—N—[(R)-2-(3-butoxy-3-o-tolylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]-2-hydroxy-3-(1H-imidazol-4-yl)propionamide are obtained in the form of a white powder with a yield of 13%.

Workup

  1. stirringthe mixture is stirred for 72 h at ambient temperature
  2. extractionthe medium is extracted with a 20/80 heptane/ethyl acetate mixture
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by preparative thin layer chromatography (eluent: 90/10 dichloro-methane/methanol)

Sources & evidence

ORD record
ord-1c84c1bd1a514fbda709b74b9eb704f3
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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