Trifluoroacetic acid → HCID 9916482, compound

HRID 1274541Notes

Reaction equation

HRID 1274541 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13]([CH2:15][N:16]([CH2:33][C:34](=[O:48])[NH:35][CH2:36][C:37]2[CH:42]=[CH:41][C:40]([C:43](=[O:46])[NH:44][OH:45])=[C:39]([OH:47])[CH:38]=2)[C:17](=[O:32])[CH2:18][CH2:19][CH2:20][C:21]([NH:23][NH:24]C(OC(C)(C)C)=O)=[O:22])=[O:14])=[CH:7][C:6]=1[OH:49])=[O:4].FC(F)(F)C(O)=O>ClC(Cl)C>[OH:45][NH:44][C:43]([C:40]1[CH:41]=[CH:42][C:37]([CH2:36][NH:35][C:34]([CH2:33][N:16]([CH2:15][C:13](=[O:14])[NH:12][CH2:11][C:8]2[CH:9]=[CH:10][C:5]([C:3](=[O:4])[NH:2][OH:1])=[C:6]([OH:49])[CH:7]=2)[C:17](=[O:32])[CH2:18][CH2:19][CH2:20][C:21]([NH:23][NH2:24])=[O:22])=[O:48])=[CH:38][C:39]=1[OH:47])=[O:46]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22088379HCID 22088379, compound

Product 1

HCID 9916482HCID 9916482, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

The crude N,N-bis-({N-[(4-(N-hydroxycarbamoyl)-3-hydroxyphenyl)methyl]-carbamoyl}methyl)-N'-[(tert-butoxy)carbonylamino]pentane-1,5-diamide from above was suspended in 20 mL of dichloroethane and 10 mL of trifluoroacetic acid was added. The deprotection reaction was stirred for 4 hours at room temperature. Dichloroethane and trifluoroacetic acid were removed in vacuo, and the resulting residue was dissolved in 10 mL of methanol, which was added dropwise to 150 mL of stirred ethyl acetate. A precipitate formed which was collected by filtration, washed with ethyl acetate and then dried in vacuo under a high vacuum. Obtained 1.41 grams (68% yield) of product as a white powder.

Workup

  1. customThe deprotection reaction
  2. customDichloroethane and trifluoroacetic acid were removed in vacuo
  3. dissolutionthe resulting residue was dissolved in 10 mL of methanol
  4. additionwhich was added dropwise to 150 mL of stirred ethyl acetate
  5. customA precipitate formed which
  6. filtrationwas collected by filtration
  7. washwashed with ethyl acetate
  8. customdried in vacuo under a high vacuum

Sources & evidence

ORD record
ord-36725a13067e4225b3555b2e0c38ac79
Source dataset
uspto-grants-2000_12
Patent number
US06156884

Reaction notes

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