Trifluoroacetic acid → HCID 11675907, compound

HRID 1295522Notes

Reaction equation

HRID 1295522 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:42])([C:23]1[NH:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:30][CH:29]=2)=[CH:26][N:27]=1)[CH2:9][O:10][P:11]([O:18]C(C)(C)C)([O:13]C(C)(C)C)=[O:12])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.CCOCC>[NH2:7][C:8]([C:23]1[NH:24][C:25]([C:28]2[CH:29]=[CH:30][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:32][CH:33]=2)=[CH:26][N:27]=1)([CH3:42])[CH2:9][O:10][P:11](=[O:12])([OH:18])[OH:13]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68844761HCID 68844761, compound

Product 1

HCID 11675907HCID 11675907, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 8 (22 mg, 0.035 mmol) in CH2Cl2 (1 mL) was added trifluoroacetic acid (1 mL) and stirring was continued 4 h. Solvent and excess trifluoroacetic acid were removed in vacuo to afford a brown oil. The oil was diluted with ether and concentrated in vacuo 5 times on a rotary evaporator to afford a white solid which was placed in a fritted funnel and washed with cold ether producing VPC24287 (13 mg, 91%) as a powdery white solid. Rf=0 (4:1 CHCl3/methanol).

Workup

  1. customSolvent and excess trifluoroacetic acid were removed in vacuo
  2. customto afford a brown oil
  3. concentrationconcentrated in vacuo 5 times on a rotary evaporator
  4. customto afford a white solid which
  5. customwas placed in a fritted funnel
  6. washwashed with cold ether producing VPC24287 (13 mg, 91%) as a powdery white solid

Sources & evidence

ORD record
ord-e1802c371a3346afa4a7286dadfa6238
Source dataset
uspto-grants-2007_07
Patent number
US07241790B2

Reaction notes

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