Trifluoroacetic acid → [1-{(2-Amino-ethyl)-[(2-methyl-2-phenyl-propylcarbamoyl)-methyl]-carbamoyl}-2-(3H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester

HRID 841145Notes

Reaction equation

HRID 841145 reaction equation
[CH2:1]([O:8][C:9](=[O:64])[NH:10][C@H:11]([C:37](=[O:63])[N:38]([CH2:53][CH2:54][NH:55]C(OC(C)(C)C)=O)[CH2:39][C:40](=[O:52])[NH:41][CH2:42][C:43]([CH3:51])([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH3:44])[CH2:12][C:13]1[N:14]=[CH:15][N:16](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[CH2:1]([O:8][C:9](=[O:64])[NH:10][CH:11]([C:37](=[O:63])[N:38]([CH2:53][CH2:54][NH2:55])[CH2:39][C:40](=[O:52])[NH:41][CH2:42][C:43]([CH3:44])([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH3:51])[CH2:12][C:13]1[NH:14][CH:15]=[N:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70169971(S)[1-{(2-tert-Butoxycarbonylamino-ethyl)-[(2-methyl-2-phenyl-propylcarbamoyl)-methyl]-carbamoyl}-2-(1-trityl-1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester

Product 1

HCID 18717562[1-{(2-Amino-ethyl)-[(2-methyl-2-phenyl-propylcarbamoyl)-methyl]-carbamoyl}-2-(3H-imidazol-4-yl)-ethyl]-carbamic acid benzyl esterYield 45%

Procedure

The compound from Step 4 (1.09 g, 1.26 mmol) was treated with 95% aqueous trifluoroacetic acid (50 mL) for 1 hour at room temperature. The solvent was reduced to a few milliliters, and pipetted into 200 mL of ether/hexanes. The product was allowed to precipitate overnight at −40° C. The solid was collected, rinsed and dried. Purification was carried out via reversed-phase HPLC (0.1% trifluoroacetic acid in acetonitrile and 0.1% aqueous trifluoroacetic acid as eluent; C-18 column) to give a white powder; 0.30 g (45% yield). MS-APCI: M+1=521.2.

Workup

  1. customto precipitate overnight at −40° C
  2. customThe solid was collected
  3. washrinsed
  4. customdried
  5. customPurification
  6. customto give a white powder

Sources & evidence

ORD record
ord-9c822c8eda72419999364d2e74b72d9b
Source dataset
uspto-grants-2002_04
Patent number
US06369034B1

Reaction notes

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