Ammonia → tert-butyl N-(1-carbamoylcyclopropyl)carbamate

HRID 586132Notes

Reaction equation

HRID 586132 reaction equation
[C:1](C1CC1(N)C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([N:17](CC)CC)C.C(OC(Cl)=O)C.[NH3:28].[CH2:29]1[CH2:33][O:32][CH2:31][CH2:30]1>O1CCOCC1>[C:4]([O:3][C:1](=[O:2])[NH:28][C:29]1([C:33](=[O:32])[NH2:17])[CH2:30][CH2:31]1)([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 200413171-Amino-2-(tert-butoxycarbonyl)cyclopropane-1-carboxylic acid

Product 1

HCID 20825554tert-butyl N-(1-carbamoylcyclopropyl)carbamateYield 72.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of Boc-1-aminocyclopropane-1-carboxylic acid (25 g, 124 mmol) and triethylamine (19 mL, 1.1 equivalent) in THF (200 mL) at −10° C. ethylchloroformate (13 mL, 1.1 equivalent) was added slowly. The mixture was stirred at this temperature for 20 min before a solution of ammonia in 1,4-dioxane (0.5 M, 300 mL) was added. It was allowed to warm to room temperature and stirred overnight. It was concentrated, diluted with water, extracted with dichloromethane, washed with brine, dried (sodium sulfate), concentrated again and dried to give (1-carbamoyl-cyclopropyl)-carbamic acid tert-butyl ester (18 g, 72.5%).

Workup

  1. additionwas added
  2. concentrationIt was concentrated
  3. additiondiluted with water
  4. extractionextracted with dichloromethane
  5. washwashed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated again
  8. customdried

Sources & evidence

ORD record
ord-3132e197b0da4a7cb748d034b2b5fbb0
Source dataset
uspto-grants-2005_08
Patent number
US06936606B2

Reaction notes

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