isobutyl 2-(4-((1E,4E)-2-(tert-butoxycarbonylamino)-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)phenyl)acetate → HCID 50943617, compound

HRID 2364642Notes

Reaction equation

HRID 2364642 reaction equation
C(OC([NH:8][C:9]1[CH2:10][C:11]([C:34](=[O:50])[N:35]([CH2:39][CH2:40][CH2:41][O:42][Si](C(C)(C)C)(C)C)[CH2:36][CH2:37][CH3:38])=[CH:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[O:28])=[CH:22][CH:21]=3)=[CH:16][C:14]=2[N:15]=1)=O)(C)(C)C>ClCCl.C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[CH2:10][C:11]([C:34](=[O:50])[N:35]([CH2:39][CH2:40][CH2:41][OH:42])[CH2:36][CH2:37][CH3:38])=[CH:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][C:23]([CH2:26][C:27]([O:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[O:28])=[CH:24][CH:25]=3)=[CH:16][C:14]=2[N:15]=1

Participants

4

Reactant 1

HCID 66960424isobutyl 2-(4-((1E,4E)-2-(tert-butoxycarbonylamino)-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)phenyl)acetate

Product 1

HCID 50943617HCID 50943617, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Isobutyl 2-(4-((1E,4E)-2-(tert-butoxycarbonylamino)-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)phenyl)acetate) was dissolved in 2 mls of dichloromethane and 0.5 ml of TFA. After about one hour, the mixture was concentrated under reduced pressure and the resulting residue was then re-dissolved in dichloromethane and 1 ml of concentrated ammonium hydroxide added and the mixture vigorously stirred for 15 minutes. This mixture was then diluted with water, extracted with dichloromethane (2×), extracts dried over sodium sulfate and concentrated under reduced pressure. Preparative thin layer chromatography (2×0.5 mm plates, 10% MeOH/DCM/0.5% NH4OH) afforded isobutyl 2-(4-((1E,4E)-2-amino-4-((3-hydroxypropyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)phenyl)acetate. 1H NMR (400 MHz, CDCl3) δ 7.27-7.39 (m, 5H), 7.19-7.21 (m, 1H), 7.01-7.06 (m, 1H), 6.87 (s, 1H), 3.80-3.85 (m, 2H), 3.58-3.69 (m, 6H), 3.46-3.53 (m, 2H), 2.82 (s, 2H), 1.80-1.89 (m, 3H), 1.66-1.75 (m, 2H), 0.90-0.98 (m, 3H), 0.81-0.87 (m, 6H); m/z (APCI-pos) M+1=492.3.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was then re-dissolved in dichloromethane
  3. addition1 ml of concentrated ammonium hydroxide added
  4. additionThis mixture was then diluted with water
  5. extractionextracted with dichloromethane (2×)
  6. dry with materialextracts dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0610b7cb67d443a281b2be9ec541e5dc
Source dataset
uspto-grants-2014_04
Patent number
US08691809B2

Reaction notes

Loading…