Trifluoroacetic acid → HCID 9916482, compound

HRID 985183Notes

Reaction equation

HRID 985183 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-652d00d7e1f94e248c9e8232735b17d5
Source dataset
uspto-grants-2005_03
Patent number
US06870065B2

Reaction notes

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