Ammonia → (4-{4-[2-(Carbamoylmethylamino)ethoxy]phenyl}butyl)carbamic acid tert-butyl ester

HRID 1890804Notes

Reaction equation

HRID 1890804 reaction equation
C(O[C:4](=[O:28])[CH2:5][NH:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:12][CH:11]=1)C.[NH3:29]>>[C:24]([O:23][C:21](=[O:22])[NH:20][CH2:19][CH2:18][CH2:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][NH:6][CH2:5][C:4](=[O:28])[NH2:29])=[CH:15][CH:14]=1)([CH3:25])([CH3:26])[CH3:27]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 58809798{2-[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]ethylamino}acetic acid ethyl ester

Product 1

HCID 58809802(4-{4-[2-(Carbamoylmethylamino)ethoxy]phenyl}butyl)carbamic acid tert-butyl ester

Procedure

A solution of 2 (0.27 g, 0.685 mmol) dissolved in 7 N methanolic ammonia (25 mL) was stirred in a sealed tube at room temperature overnight. After this time, TLC analysis indicated that the reaction was complete. The reaction mixture was concentrated and further dried under vacuum to afford the desired product 3 (0.25 g, quantitative yield) as a yellow viscous oil which was used directly without further purification. m/z (ESI) 366.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customfurther dried under vacuum

Sources & evidence

ORD record
ord-765619b5aa6042f2bf5f3de22005d88a
Source dataset
uspto-grants-2013_08
Patent number
US08507497B2

Reaction notes

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