Trifluoroacetic acid → HCID 178521724, compound

HRID 1527365Notes

Reaction equation

HRID 1527365 reaction equation
C(OC([N:8]1[C@H:13]([C:14](=[O:28])[NH:15][C:16]2[CH:21]=[C:20]([C:22]3[NH:26][N:25]=[N:24][N:23]=3)[CH:19]=[C:18]([Br:27])[CH:17]=2)[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[Br:27][C:18]1[CH:17]=[C:16]([NH:15][C:14]([C@@H:13]2[CH2:12][C@@H:11]3[C@@H:9]([CH2:10]3)[NH:8]2)=[O:28])[CH:21]=[C:20]([C:22]2[NH:26][N:25]=[N:24][N:23]=2)[CH:19]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452531HCID 178452531, compound

Product 1

HCID 178521724HCID 178521724, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1R,3S,5R)-3-[3-bromo-5-(1H-tetrazol-5-yl)-phenylcarbamoyl]-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (200 mg, 0.445 mmol) in CH2Cl2 (2 mL) was added TFA (0.686 ml, 8.9 mmol). The reaction mixture was stirred at RT for 4 h. After completion the reaction mixture was diluted with CH2Cl2 and MeOH and the volatiles were removed under vacuum. MeOH was added and the reaction mixture concentrated again under vacuum. This operation was repeated twice to afford a mixture in a 2/3 ratio of (1R,3S,5R)-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid [3-bromo-5-(1H-tetrazol-5-yl)-phenyl]-amide: MS (LC/MS): 349.2 [M+H]+; tR (HPLC conditions k): 3.06 min and (1R,3S,5R)-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid [3-bromo-5-(1-tert-butyl-1H-tetrazol-5-yl)-phenyl]-amide: MS (LC/MS): 405.3 [M+H]+; tR (HPLC conditions k): 4.46 min.

Workup

  1. customthe volatiles were removed under vacuum
  2. additionMeOH was added
  3. concentrationthe reaction mixture concentrated again under vacuum

Sources & evidence

ORD record
ord-ba0cff67c3364443987ef713ea73c548
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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