Triethylamine → Tert-butyl n-[(phenylcarbamoyl)methyl]carbamate

HRID 1700350Notes

Reaction equation

HRID 1700350 reaction equation
Cl.CN(C)CCCN=C=NCC.O[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2N=N1.C(N(CC)CC)C.[C:30]([O:34][C:35]([NH:37][CH2:38][C:39](O)=[O:40])=[O:36])([CH3:33])([CH3:32])[CH3:31]>ClCCl.C(OCC)(=O)C>[C:18]1([NH:14][C:39]([CH2:38][NH:37][C:35](=[O:36])[O:34][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:40])[CH:17]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 10634424Tert-butyl n-[(phenylcarbamoyl)methyl]carbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.27 g (1.19 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 681 mg (5.04 mmol) of 1-hydroxybenzotriazole and 0.95 ml (6.82 mmol) of triethylamine were added to 1.15 g (6.56 mmol) of t-butoxycarbonylglycine in 20 ml of dichloromethane under cooling in an ice bath, and they were stirred at room temperature overnight. Ethyl acetate was added to the reaction mixture, and the product was washed with 0.1 N hydrochloric acid and then with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain the title compound.

Workup

  1. temperatureunder cooling in an ice bath
  2. washthe product was washed with 0.1 N hydrochloric acid
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94afdbd7c5104b669ac7bff43f1510da
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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