HCID 86652685, compound → HCID 50943785, compound

HRID 2364644Notes

Reaction equation

HRID 2364644 reaction equation
C(OC([NH:8][C:9]1[CH2:10][C:11]([C:33](=[O:49])[N:34]([CH2:38][CH2:39][CH2:40][O:41][Si](C(C)(C)C)(C)C)[CH2:35][CH2:36][CH3:37])=[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][CH2:31][F: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:33](=[O:49])[N:34]([CH2:38][CH2:39][CH2:40][OH:41])[CH2:35][CH2:36][CH3:37])=[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][CH2:31][F:32])=[O:28])=[CH:22][CH:21]=3)=[CH:16][C:14]=2[N:15]=1

Participants

4

Reactant 1

HCID 86652685HCID 86652685, compound

Product 1

HCID 50943785HCID 50943785, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2-Fluoroethyl 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 0.012 g (35%) of 2-fluoroethyl 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 7.60-7.65 (m, 2H), 7.49-7.51 (m, 1H), 7.29-7.39 (m, 4H), 6.87 (s, 1H), 4.66-4.69 (m, 1H), 4.54-4.58 (m, 1H), 4.39-4.43 (m, 1H), 4.32-4.36 (m, 1H), 3.73 (s, 2H), 3.58-3.68 (m, 4H), 3.43-3.52 (m, 2H), 1.78-1.87 (m, 2H), 1.65-1.75 (m, 2H), 0.90-0.96 (m, 3H); m/z (APCI-pos) M+1=482.2.

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-f313a654de5a4c4dbdd92b151d75e67f
Source dataset
uspto-grants-2014_04
Patent number
US08691809B2

Reaction notes

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