Trifluoroacetic acid → HCID 9938694, compound

HRID 1274540Notes

Reaction equation

HRID 1274540 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:13][NH:14][C:15]([CH2:17][N:18]([C:36](=[O:50])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][NH:42]C(OC(C)(C)C)=O)[CH2:19][C:20]([NH:22][CH2:23][C:24]2[CH:33]=[C:32]([OH:34])[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]([OH:35])[CH:25]=2)=[O:21])=[O:16])[CH:5]=[C:6]([OH:12])[C:7]=1[C:8]([O:10][CH3:11])=[O:9].FC(F)(F)C(O)=O.FC(F)(F)C([O-])=O>ClC(Cl)C>[NH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][C:36]([N:18]([CH2:19][C:20]([NH:22][CH2:23][C:24]1[CH:33]=[C:32]([OH:34])[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]([OH:35])[CH:25]=1)=[O:21])[CH2:17][C:15](=[O:16])[NH:14][CH2:13][C:4]1[CH:5]=[C:6]([OH:12])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:2]([OH:1])[CH:3]=1)=[O:50]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 84468TrifluoroacetateHCID 9896472HCID 9896472, compound

Product 1

HCID 9938694HCID 9938694, compoundYield 113%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

The methyl 4-[(2-{N-[(N-{(3,5-dihydroxy-4-(methoxycarbonyl)phenyl]methyl}-carbamoyl)methyl]-6-[(tert-butoxy)carbonylamino]hexanoylamino}acetylamino)methyl]-2,6-dihydroxybenzoate (2.31 g, 3.28 mmole) was suspended in 10 mL of dichloroethane and 2 mL of trifluoroacetic acid (26.0 mmole) was added. The deprotection reaction was stirred for 3 hours at room temperature. Dichloroethane and trifluoroacetic acid were removed in vacuo, and the resulting residue was dissolved in 20 mL of methanol, and the product precipitated by addition of ethyl ether. The product was collected by filtration, waashed with ethyl acetate and dried in vacuo under a high vacuum. Obtained 2.24 grams (97% yield) of product as the trifluoroacetate salt.

Workup

  1. customThe deprotection reaction
  2. customDichloroethane and trifluoroacetic acid were removed in vacuo
  3. dissolutionthe resulting residue was dissolved in 20 mL of methanol
  4. customthe product precipitated by addition of ethyl ether
  5. filtrationThe product was collected by filtration
  6. customdried in vacuo under a high vacuum

Sources & evidence

ORD record
ord-978912d45d80496da537508fcccfe400
Source dataset
uspto-grants-2000_12
Patent number
US06156884

Reaction notes

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