Phenyl chloroformate → tert-butyl N-[1-(4-chlorophenyl)-3-(phenoxycarbonylamino)propyl]carbamate

HRID 423117Notes

Reaction equation

HRID 423117 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][CH2:12][CH2:13][CH:14]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH:14]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:13][CH2:12][NH:11][C:2]([O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:3])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 24729697Tert-butyl 3-amino-1-(4-chlorophenyl)propylcarbamate2×

Product 1

HCID 57750354tert-butyl N-[1-(4-chlorophenyl)-3-(phenoxycarbonylamino)propyl]carbamateYield 100.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

Phenyl chloroformate (0.132 mL, 1.05 mmol) was added dropwise to tert-butyl 3-amino-1-(4-chlorophenyl)propylcarbamate (Intermediate 25) (300 mg, 1.05 mmol) and sodium bicarbonate (133 mg, 1.58 mmol) in dioxane (10 mL) at 20° C. under nitrogen. The resulting solution was stirred at 20° C. for 2 hours. The reaction mixture was concentrated and diluted with EtOAc (20 mL) and washed with water (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford tert-butyl N-[1-(4-chlorophenyl)-3-(phenoxycarbonylamino)-propyl]carbamate (427 mg, 100%) as a gum.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc (20 mL)
  3. washwashed with water (20 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6b65ea6c779e4aeda37e00d417e5a01b
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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