Tetrahydrofuran → methyl (R)-3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionate

HRID 644314Notes

Reaction equation

HRID 644314 reaction equation
[NH2:1][C@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[C:10]([CH2:16][CH3:17])[CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].C(N(C(C)C)C(C)C)C.[NH:27]1[CH2:32][CH2:31][CH:30]([N:33]2[CH2:39][CH2:38][C:37]3[CH:40]=[CH:41][CH:42]=[CH:43][C:36]=3[NH:35][C:34]2=[O:44])[CH2:29][CH2:28]1.C1C[O:48][CH2:47]C1>>[CH2:16]([C:10]1[CH:9]=[C:8]([CH2:7][C@@H:2]([NH:1][C:47]([N:27]2[CH2:28][CH2:29][CH:30]([N:33]3[CH2:39][CH2:38][C:37]4[CH:40]=[CH:41][CH:42]=[CH:43][C:36]=4[NH:35][C:34]3=[O:44])[CH2:31][CH2:32]2)=[O:48])[C:3]([O:5][CH3:6])=[O:4])[CH:13]=[CH:12][C:11]=1[CH2:14][CH3:15])[CH3:17]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 69712230methyl (R)-2-amino-3-(3,4-diethyl-phenyl)-propionate

Product 1

HCID 69711722methyl (R)-3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionate

Procedure

The mixture of 41.7 g (0.153 mol) methyl (R)-2-amino-3-(3,4-diethyl-phenyl)-propionate, 800 mL THF and 28 mL (0.161 mol) ethyldiisopropylamine was combined with 25.4 g (0.157 mol) CDT and then 38.0 g (0.155 mol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one while cooling with an ice bath and refluxed for 3 h with stirring. The reaction mixture was then extracted with 300 mL 10% citric acid solution, three times with 100 mL aliquots of water and 200 mL saturated NaCl solution, dried and evaporated down under reduced pressure.

Workup

  1. temperaturerefluxed for 3 h
  2. extractionThe reaction mixture was then extracted with 300 mL 10% citric acid solution, three times with 100 mL aliquots of water and 200 mL saturated NaCl solution
  3. customdried
  4. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-06478303c98c400fb5e378355326595e
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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