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

HRID 1509862Notes

Reaction equation

HRID 1509862 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-03858751f56048d0814a5f22c10fbc33
Source dataset
uspto-grants-2012_07
Patent number
US08211895B2

Reaction notes

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