Water → HCID 69412358, compound

HRID 1766389Notes

Reaction equation

HRID 1766389 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH:18][CH:19]2[CH:26]3[CH:22]([CH2:23][N:24](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:25]3)[CH2:21][CH2:20]2)=[O:17])[CH:6]=[C:7]([C:9]2[N:13]([CH3:14])[N:12]=[N:11][N:10]=2)[CH:8]=1)[CH3:2].O>FC(F)(F)C(O)=O>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH:18][CH:19]2[CH:26]3[CH:22]([CH2:23][NH:24][CH2:25]3)[CH2:21][CH2:20]2)=[O:17])[CH:6]=[C:7]([C:9]2[N:13]([CH3:14])[N:12]=[N:11][N:10]=2)[CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 69411921HCID 69411921, compound

Product 1

HCID 69412358HCID 69412358, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-[3-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-N′-[(3aRS,4RS,6aSR)-2-trityloctahydrocyclo-penta[c]pyrrol-4-yl]urea (310 mg, 518 μmol) was dissolved in trifluoroacetic acid (5 mL) to provide a bright yellow solution. This was treated dropwise with water (5 mL) to provide a pale yellow slurry. After 2 hours, the mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate and 1.0 N aqueous hydrochloric acid. The aqueous phase was washed with additional ethyl acetate, and then made strongly basic with 50% aqueous sodium hydroxide. The resulting mixture was extracted three times with ethyl acetate, and these organic phases were combined, dried over sodium sulfate, and concentrated under vacuum to provide a white glass (167 mg, 90%). NMR (300 MHz, CDCl3) δ7.71 (s, 1H), 7.69 (s, 1H), 7.29 (s, 1H), 7.18 (s, 1H), 6.49 (d, J=8 Hz, 1H), 4.27 (m, 1H), 4.20 (s, 3H), 2.97 (m, 2H), 2.8-2.6 (m, 6H), 1.90 (m, 1H), 1.70 (m, 2H), 1.36 (m, 1H), 1.24 (t, J=7 Hz, 3H).

Workup

  1. customto provide a bright yellow solution
  2. customto provide a pale yellow slurry
  3. concentrationthe mixture was concentrated under vacuum
  4. customThe residue was partitioned between ethyl acetate and 1.0 N aqueous hydrochloric acid
  5. washThe aqueous phase was washed with additional ethyl acetate
  6. extractionThe resulting mixture was extracted three times with ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a547305f1fad49489cff7ef5ef0968d7
Source dataset
uspto-grants-2007_06
Patent number
US07230022B2

Reaction notes

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