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Tetrabutylammonium Fluoride → (4R,5R,6R)-5-Acetylamino-4-hydroxy-6-(phenethylpropylcarbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

HRID 1604000
Notes
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Reaction equation

HRID 1604000 reaction equation
[C:1]([NH:4][C@H:5]1[C@H:10]([C:11](=[O:24])[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:9][C:8]([C:25]([O:27]C)=[O:26])=[CH:7][C@H:6]1[O:29][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([NH:4][C@H:5]1[C@H:10]([C:11](=[O:24])[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:9][C:8]([C:25]([OH:27])=[O:26])=[CH:7][C@H:6]1[OH:29])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86754844(4R,5S,6R)-5-acetylamino-4-(tert-butyldiphenylsilanyloxy)-6-(phenethylpropylcarbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid, methyl ester

Product 1

HCID 70196688(4R,5R,6R)-5-Acetylamino-4-hydroxy-6-(phenethylpropylcarbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acidYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a stirred solution of (4R,5S,6R)-5-acetylamino-4-(tert-butyldiphenylsilanyloxy)-6-(phenethylpropylcarbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid, methyl ester (7 g) in tetrahydrofuran (70 ml) was added tetra-n-butylammonium fluoride (12 ml of a 1M solution in tetrahydrofuran). After 4 hours at 23° C. the solvent was removed in vacuo and the residue was partitioned between brine and ethyl acetate. The organic extracts were dried over anhydrous sodium sulphate and the solvent was removed in vacuo to give an oil. This was chromatographed over silica (Merck 9385, 700 ml) using medium pressure (ca 4 psi) and dichloromethane/methanol (95:5 v/v) as eluant. The required fractions were combined and the solvent removed in vacuo to give the title compound as a pale yellow foam (3.98 g). 1H NMR (250MHz, CDCl3, rotamers) 7.3 (5H,m), 6.2 (1H, 2×d, J=4Hz), 5.1+4.9 (1H,2×d, J=6Hz), 4.6+4.5 (1H, 2×m), 4.4--4.2 (1H,2× m), 3.8 (3H, 2×s), 3.7--3.3 (4H, m), 3.0+2.8 (2H, 2×m), 2.0 (3H, 2×s), 1.8--1.3 (2H, m), 0.9 (3H, m); Mass spec. (low resolution) MH+ =405.

Workup

  1. customAfter 4 hours at 23° C. the solvent was removed in vacuo
  2. customthe residue was partitioned between brine and ethyl acetate
  3. dry with materialThe organic extracts were dried over anhydrous sodium sulphate
  4. customthe solvent was removed in vacuo
  5. customto give an oil
  6. customThis was chromatographed over silica (Merck 9385, 700 ml)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-86f0b6dc4fb645bcab5de26522dfa4d2
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05990156

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes