1,2-Dichloroethane → 1-Tert-butoxycarbonylamino-1-cyclopentanecarboxamide

HRID 2201150Notes

Reaction equation

HRID 2201150 reaction equation
[C:1]([NH:8][C:9]1([C:14]([OH:16])=O)[CH2:13][CH2:12][CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=C2[N:23]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[C:14]([C:9]1([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:16])[NH2:23]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 27346451-tert-Butoxycarbonylaminocyclopentanecarboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 106808671-Tert-butoxycarbonylamino-1-cyclopentanecarboxamideYield 59.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-Boc-1-amino-1-cyclopentane carboxylic acid (518 mg, 2.26 mmol) and HOBt hydrate (416 mg, 2.71 mmol) in DMF (5 mL), EDC (522 mg, 2.71 mmol) was added. After being stirred at room temperature for 1 h, conc. NH4OH (14 N, 0.900 mL, 12.6 mmol) was added. The mixture was stirred for 18 h. Water and EtOAc were added. The organic phase was washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give tert-butyl 1-carbamoylcyclopentylcarbamate (305 mg).

Workup

  1. stirringThe mixture was stirred for 18 h
  2. washThe organic phase was washed with 5% NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ecafee7988e44ff7bf4132038c808778
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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