Acetic Acid → HCID 59997325, compound

HRID 1815567Notes

Reaction equation

HRID 1815567 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([N:13]([CH2:50][CH:51]([CH3:53])[CH3:52])[CH2:14][C@@H:15]([OH:49])[C@@H:16]([NH:37][C:38](=[O:48])[O:39][C@@H:40]3[C@H:47]4[C@H:43]([O:44][CH2:45][CH2:46]4)[O:42][CH2:41]3)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][Si](C(C)(C)C)(C)C)=[CH:20][CH:19]=3)(=[O:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([N:13]([CH2:50][CH:51]([CH3:53])[CH3:52])[CH2:14][C@@H:15]([OH:49])[C@@H:16]([NH:37][C:38](=[O:48])[O:39][C@@H:40]3[C@H:47]4[C@H:43]([O:44][CH2:45][CH2:46]4)[O:42][CH2:41]3)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])=[CH:20][CH:19]=3)(=[O:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11078149TBAF tetrahydrofuranHCID 59997260HCID 59997260, compound

Product 1

HCID 59997325HCID 59997325, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-[4-(4-{[tert-butyl(dimethyl)silyl]oxy}butoxy)benzyl]-2-hydroxypropylcarbamate (0.38 g, 0.48 mmol) in tetrahydrofuran (5 mL) at 0° C. was added a 1:1 mixture of 1M tetra-n-butyl ammonium fluoride/tetrahydrofuran and acetic acid (1.2 mL) and the mixture was stirred at ambient temperature for 18 h. The mixture was diluted with ethyl acetate and washed with water (4×), dried (sodium sulfate) and evaporated. The resulting solid was triturated with diethyl ether and filtered to afford the title compound as a white solid (0.24 g). 1H NMR (DMSO-d6): δ 0.78 (3H, d), 0.82 (3H, d), 1.2 (1H ,dd), 1.38 (1H, quintuplet), 1.5 (2H, quintuplet), 1.65 (2H, quintuplet), 1.9-2.0 (1H, m), 2.18 (1H, t), 2.7-2.8 (3H, m), 2.9 (1H, d), 2.97 (1H, dd), 3.20-3.25 (1H, m), 3.38 (2H, t), 3.4-3.5 (1H, m), 3.52-3.62 (3H, m), 3.7 (1H, t), 3.8 (1H, dd), 3.93 (2H, t), 4.2 (1H, br s), 4.8 (1H, dt), 5.0 (1H, d), 5.5 (1H, d), 6.18 (2H, s), 6.78 (2H, d), 7.0-7.1 (3H, m), 7.2 (1H, d), 7.26 (1H, s), 7.3 (1H, d); MS: 665 (MH+)

Workup

  1. washwashed with water (4×)
  2. dry with materialdried (sodium sulfate)
  3. customevaporated
  4. customThe resulting solid was triturated with diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-92fe0934e6e74a9487e21e5e9befb0b5
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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