Trifluoroacetic acid → HCID 131720394, compound

HRID 726427Notes

Reaction equation

HRID 726427 reaction equation
C[O:2][C:3](=[O:40])[C@@H:4]([NH:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:33])=[O:32])[CH2:5][NH:6][C:7](=[O:29])[CH2:8][CH2:9][NH:10][C:11](=[O:28])[C:12]1[CH:17]=[CH:16][C:15]([C:18](=[NH:27])[NH:19]C(OC(C)(C)C)=O)=[CH:14][CH:13]=1.[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]>>[OH:47][C:41]([C:43]([F:46])([F:45])[F:44])=[O:42].[C:18]([C:15]1[CH:16]=[CH:17][C:12]([C:11]([NH:10][CH2:9][CH2:8][C:7]([NH:6][CH2:5][C@H:4]([NH:30][S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:33])=[O:32])[C:3]([OH:40])=[O:2])=[O:29])=[O:28])=[CH:13][CH:14]=1)(=[NH:19])[NH2:27]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 140386031HCID 140386031, compound

Product 1

HCID 131720394HCID 131720394, compound

Procedure

The product (0.385 g) obtained in the above (8) is dissolved in TFA (5 ml) under ice-cooling, and the mixture is stirred for 30 minutes, and then stirred at room temperature for one hour. The TFA is distilled off, and a mixture of acetic acid (2 ml) and water (8 ml) is added to the residue, and the mixture is refluxed for 11 hours. The reaction mixture is concentrated under reduced pressure, and the residue is purified by HPLC to give the desired compound (97 mg) as a white powder.

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature for one hour
  3. distillationThe TFA is distilled off
  4. additiona mixture of acetic acid (2 ml) and water (8 ml)
  5. additionis added to the residue
  6. temperaturethe mixture is refluxed for 11 hours
  7. concentrationThe reaction mixture is concentrated under reduced pressure
  8. customthe residue is purified by HPLC

Sources & evidence

ORD record
ord-ac532d842b224b40ba2097770f21675a
Source dataset
uspto-grants-1998_01
Patent number
US05707994

Reaction notes

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