Methanol → HCID 59432352, compound

HRID 507022Notes

Reaction equation

HRID 507022 reaction equation
[CH2:1](P(CCCC)CCCC)CCC.[F:14][C:15]([F:52])([F:51])[C:16]1[CH:17]=[C:18]([CH:44]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:46]=1)[CH2:19][N:20]([C:39]1[N:40]=[N:41][NH:42][N:43]=1)[CH:21]1[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])[C:23]2[CH:34]=[CH:35][C:36]([Br:38])=[CH:37][C:22]1=2.CO>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:50][C:47]([F:48])([F:49])[C:45]1[CH:44]=[C:18]([CH:17]=[C:16]([C:15]([F:14])([F:51])[F:52])[CH:46]=1)[CH2:19][N:20]([C:39]1[N:40]=[N:41][N:42]([CH3:1])[N:43]=1)[CH:21]1[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])[C:23]2[CH:34]=[CH:35][C:36]([Br:38])=[CH:37][C:22]1=2

Participants

6

Reactant 3

HCID 887MethanolHCID 13831TributylphosphineHCID 59432334HCID 59432334, compound

Product 1

HCID 59432352HCID 59432352, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add tri-n-butylphosphine to a solution of (+/−)-isopropyl 5-[(3,5-bistrifluoromethylbenzyl)-(2H-tetrazol-5-yl)amino]-7-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate, methanol and 1,1′-(azocarbonyl)dipiperidine (ADDP) in toluene at 0° C. under nitrogen and warm to room temperature. Dilute the mixture with ethyl acetate, wash with 2 N HCl and brine and dry over sodium sulfate. Remove the solvents under reduced pressure and purify the residue by flash column chromatography on silica gel to provide the title compound.

Workup

  1. washwash with 2 N HCl and brine
  2. dry with materialdry over sodium sulfate
  3. customRemove the solvents under reduced pressure
  4. custompurify the residue by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-64178193d377480593c5702101bae704
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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