Diisopropylethylamine → Tert-butyl 4-(4-(1-(benzyloxycarbonyl)azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate

HRID 873558Notes

Reaction equation

HRID 873558 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]([OH:17])=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.[NH2:29][C:30]1[CH:49]=[CH:48][C:33]([O:34][CH:35]2[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]2)=[CH:32][CH:31]=1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]([C:15]([NH:29][C:30]2[CH:31]=[CH:32][C:33]([O:34][CH:35]3[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:42])[CH2:37][CH2:36]3)=[CH:48][CH:49]=2)=[O:17])[CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 109882141-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acidHCID 22181157tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

Product 1

HCID 86702035Tert-butyl 4-(4-(1-(benzyloxycarbonyl)azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(Benzyloxycarbonyl)azetidine-3-carboxylic acid (5.10 g, 21.67 mmol), 1-hydroxybenzotriazole hydrate (4.15 g, 27.1 mmol) and tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate (5.28 g, 18.06 mmol) were suspended in dimethylformamide (25 ml) followed by addition of diisopropylethylamine (9.64 ml, 54.2 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (5.19 g, 27.1 mmol). The mixture was stirred at room temperature overnight and the solution was diluted with water. The resulting turbid mixture was extracted with ethyl acetate and then ethyl acetate/tetrahydrofuran. The organics were combined and dried over magnesium sulfate, filtered and concentrated to give a solid which was triturated with ether and filtered to give the title compound.

Workup

  1. extractionThe resulting turbid mixture was extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a solid which
  6. customwas triturated with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-3dcd7e33004249a4a81e5060ad578230
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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