Ammonium Hydroxide → cis-3-(Boc-amino)cyclopentanecarboxamide

HRID 2404392Notes

Reaction equation

HRID 2404392 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O[N:19]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[OH-].[NH4+]>ClCCl.O>[C:14]([C@@H:11]1[CH2:12][CH2:13][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10]1)(=[O:16])[NH2:19]

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 52247453-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid

Product 1

HCID 59028693cis-3-(Boc-amino)cyclopentanecarboxamideYield 43.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of racemic (1R,3S)-3-(tert-butoxycarbonylamino)cyclopentane-carboxylic acid (AMRI, 3.9 g, 17.0 mmol) in dichloromethane (100 mL) was added 1-hydroxybenzotriazole monohydrate (3.1 g, 20.4 mmol), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (4.7 g, 24.7 mmol) and ammonium hydroxide (19.9 g, 170 mmol). The reaction mixture was stirred at room temperature for 16 h and then diluted with water (20 mL). The aqueous layer was extracted with dichloromethane (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was triturated in 50 mL of 1:1 ethyl acetate/hexanes and collected by filtration to obtain 1.7 g of the title compound. MS (ESI+) M/Z 228 [M+H]+.

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (3×20 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated in 50 mL of 1:1 ethyl acetate/hexanes
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-daebab2458854057a3a4f25e3f9955de
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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