Trifluoroacetic acid → HCID 6321070, compound

HRID 1815542Notes

Reaction equation

HRID 1815542 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([N:13]([CH2:48][CH:49]([CH3:51])[CH3:50])[CH2:14][C@@H:15]([OH:47])[C@@H:16]([NH:35][C:36](=[O:46])[O:37][C@@H:38]3[C@H:45]4[C@H:41]([O:42][CH2:43][CH2:44]4)[O:40][CH2:39]3)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][NH:27]C(OC(C)(C)C)=O)=[CH:20][CH:19]=3)(=[O:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:27][CH2:26][CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][C@H:16]([NH:35][C:36](=[O:46])[O:37][C@@H:38]2[C@H:45]3[C@H:41]([O:42][CH2:43][CH2:44]3)[O:40][CH2:39]2)[C@H:15]([OH:47])[CH2:14][N:13]([S:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)(=[O:11])=[O:12])[CH2:48][CH:49]([CH3:51])[CH3:50])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57945086HCID 57945086, compound

Product 1

HCID 6321070HCID 6321070, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.65 g (0.89 mmol) of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}benzyl)-2-hydroxypropylcarbamate in 10 mL of anhydrous CH2Cl2 was treated with 15 mL of TFA and the resulting solution was stirred at RT. After 2 hours the solution was evaporated at reduced pressure and the residue redissolved in CH2Cl2. The solution was washed with 0.5 M aqueous NaOH (1×), water (2×), dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 95:5 CH2Cl2/2M NH3 in MeOH) to afford 0.40 g (70%) of the desired compound as a white foam. 1H NMR (CDCl3): 7.39 (dd, 1H), 7.12 (s, 1H), 7.08 (d, 2H), 6.84 (d, 1H), 6.77 (d, 2H), 6.03 (s, 2H), 5.61 (d, 1H), 4.95 (m, 2H), 4.00-3.60 (m, 8H), 3.16-2.62 (m, 10H), 2.20-1.40 (m, 5H), 0.90 (d, 3H), 0.82 (d, 3H). MS(ESI): 636(M+H).

Workup

  1. customAfter 2 hours the solution was evaporated at reduced pressure
  2. dissolutionthe residue redissolved in CH2Cl2
  3. washThe solution was washed with 0.5 M aqueous NaOH (1×), water (2×)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (SiO2, 95:5 CH2Cl2/2M NH3 in MeOH)

Sources & evidence

ORD record
ord-8a97e8304fe8485d9765783a07166ceb
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

Loading…