1,2-Dichloroethane → tert-butyl[(R)-1-(4-methoxy-benzyl)-2-oxo-2-(3-pentyloxy-3-o-tolylazetidin-1-yl)ethyl]carbamate

HRID 540376Notes

Reaction equation

HRID 540376 reaction equation
C(O[C@:6]([N:19]=[C:20]=[O:21])([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:7]([OH:9])=O)(C)(C)C.[CH2:22](Cl)[CH2:23]Cl.[CH:26]1[CH:27]=[CH:28][C:29]2N(O)N=N[C:30]=2[CH:31]=1.F[C:37](F)(F)[C:38]([OH:40])=O.C([O:48][C:49]1([C:53]2C=CC=CC=2)[CH2:52]N[CH2:50]1)CCCC.CCN([CH:65]([CH3:67])[CH3:66])C(C)C.C[N:69]([CH:71]=O)[CH3:70]>>[C:49]([O:48][C:20](=[O:21])[NH:19][C@H:6]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)[C:7](=[O:9])[N:69]1[CH2:70][C:38]([O:40][CH2:67][CH2:65][CH2:66][CH2:22][CH3:23])([C:37]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:26])[CH2:71]1)([CH3:53])([CH3:52])[CH3:50]

Participants

7

Reactant 6

HCID 111,2-DichloroethaneHCID 6228Dimethylformamide2×HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669889253-Pentoxy-3-phenylazetidine trifluoroacetateHCID 87226379(R)-2-tert-butoxy-carbonylamino-3-(4-methoxyphenyl)propionic acid

Product 1

HCID 131731973tert-butyl[(R)-1-(4-methoxy-benzyl)-2-oxo-2-(3-pentyloxy-3-o-tolylazetidin-1-yl)ethyl]carbamateYield 56%

Procedure

2.93 g (9.93 mmol) of (R)-2-tert-butoxy-carbonylamino-3-(4-methoxyphenyl)propionic acid are dissolved in 10 ml of DMF. 2.08 g (10.9 mmol) of EDC, 1.47 g (10.9 mmol) of HOBt and a solution of 3.45 g (9.93 mmol) of 3-pentoxy-3-phenylazetidine trifluoro-acetate in 15 ml of DMF are then added. 7 ml (40.2 mmol) of DIEA are added. The reaction medium is stirred at ambient temperature for 2 h 30 and then extracted with ethyl acetate. The organic phase is washed with 1N sodium hydroxide and then dried over magnesium sulphate, filtered and evaporated. The crude product obtained is purified by silica gel chromatography (eluent 6/4 heptane/ethyl acetate). 2.83 g in the form of a white powder are obtained with a yield of 56%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with 1N sodium hydroxide
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7bbfae16ca6642b18548a117e1868995
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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