Potassium Carbonate → HCID 23382081, compound

HRID 1281187Notes

Reaction equation

HRID 1281187 reaction equation
[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N:13]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:14][C@H:15]([OH:31])[C@@H:16]([NH:24]C(=O)C(F)(F)F)[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:8][CH:7]=2)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[CH:8][C:9]([CH2:12][N:13]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:14][C@H:15]([OH:31])[C@@H:16]([NH2:24])[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:10][CH:11]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23382083HCID 23382083, compound

Product 1

HCID 23382081HCID 23382081, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.756 g (1.38 mmol) of 1-[p-(1,2,4-triazol-4-yl)phenyl]-4(S)-hydroxy-2-(tert-butyloxycarbonyl)amino-5(S)-(trifluoroacetyl)amino-6-phenyl-2-azahexane (Example 14d) is initially introduced in 28 ml of methanol, and 6.9 ml (6.89 mmol) of a 1 M aqueous solution of potassium carbonate are then added. The reaction mixture is stirred under reflux for 3 h and then concentrated down to about 10 ml; it is then acidified with dilute hydrochloric acid and extracted with methylene chloride. The title compound crystallizes out on concentrating. HPLC20-100: tret=8.97. 1H NMR (CD3OD; 200 MHz) i.a.: 8.98/s (2H); 7.75-7.6/m (4H); 7.5-7.1/m (5H); 3.96/bs (2H); 1.32/s (9H).

Workup

  1. temperatureunder reflux for 3 h
  2. concentrationconcentrated down to about 10 ml
  3. extractionextracted with methylene chloride
  4. customThe title compound crystallizes out
  5. concentrationon concentrating

Sources & evidence

ORD record
ord-b1262edab796412496295bb0215947a6
Source dataset
uspto-grants-2002_09
Patent number
US06451973B1

Reaction notes

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