Trifluoroacetic acid → HCID 59065883, compound

HRID 25742Notes

Reaction equation

HRID 25742 reaction equation
[Si]([O:8][C@H:9]1[C@@H:13]([O:14][Si](C(C)(C)C)(C)C)[C@H:12]([N:22]2[CH:27]=[CH:26][C:25](=[O:28])[NH:24][C:23]2=[O:29])[O:11][CH:10]1[C@H:30]([OH:62])[C@@H:31]([C:55]([O:57]C(C)(C)C)=[O:56])[NH:32][CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:54])[C@H:38]([CH2:50][CH:51]([CH3:53])[CH3:52])[NH:39][C:40](=[O:49])[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(C(C)(C)C)(C)C.FC(F)(F)C(O)=O>O>[O:29]=[C:23]1[NH:24][C:25](=[O:28])[CH:26]=[CH:27][N:22]1[C@@H:12]1[O:11][CH:10]([C@H:30]([OH:62])[C@@H:31]([C:55]([OH:57])=[O:56])[NH:32][CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:54])[C@H:38]([CH2:50][CH:51]([CH3:53])[CH3:52])[NH:39][C:40](=[O:49])[O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@@H:9]([OH:8])[C@H:13]1[OH:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59065937HCID 59065937, compound

Product 1

HCID 59065883HCID 59065883, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

By using an analogous procedure to that described for Example 47, tert-butyl (5S,12S)-12-[(R)-[(3R,4R,5R)-3,4-bis[tert-butyl(dimethyl)silyl]oxy}-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl](hydroxy)methyl]-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (123 mg, 0.136 mmol, obtained from Example 6), trifluoroacetic acid (5 ml) and water (6 drops) were stirred for 10 hours at room temperature. The volatiles were removed and the residue was azeotroped with toluene. The resulting residue was purified by preparative HPLC (20×250 mm YMC-ODS column eluted with 10-70% acetonitrile in water containing 0.02% trifluoroacetic acid over 49 minutes) to provide (5S,12S)-12-[(R)-[(3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-3,4-dihydroxy-tetrahydro-2-furanyl](hydroxy)methyl]-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oic acid (13 mg, 15%) as a white solid.

Workup

  1. customThe volatiles were removed
  2. customthe residue was azeotroped with toluene
  3. customThe resulting residue was purified by preparative HPLC (20×250 mm YMC-ODS column eluted with 10-70% acetonitrile in water containing 0.02% trifluoroacetic acid over 49 minutes)

Sources & evidence

ORD record
ord-ebdf29c291ba47129182c02e5a7edd1d
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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