Water → HCID 492429, compound

HRID 1604007Notes

Reaction equation

HRID 1604007 reaction equation
[N:1]([C@@H:4]1[C@@H:9]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[C@H:8]([C:17](=[O:25])[N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[O:7][C:6]([C:26]([O:28]C)=[O:27])=[CH:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(N(CC)CC)C>O1CCCC1>[NH2:1][C@@H:4]1[C@@H:9]([NH:10][C:11](=[O:16])[C:12]([F:14])([F:13])[F:15])[C@H:8]([C:17](=[O:25])[N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[O:7][C:6]([C:26]([OH:28])=[O:27])=[CH:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86754852HCID 86754852, compound

Product 1

HCID 492429HCID 492429, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (4S,5R,6R)-4-azido-6-(dipropylcarbamoyl)-5-(2,2,2-trifluoroacetylamino)-5,6-dihydro-4H-pyran-2-carboxylic acid, methyl ester (1 g) in dry tetrahydrofuran (10 ml) was added triphenylphosphine (0.75 g) and the reaction was stirred under nitrogen at 23° C. for 1.5 hours. To this was added water (2 ml) and triethylamine (2 ml) and the mixture was stirred for 16 hours at 23° C. The solvent was removed in vacuo and the residue was chromatographed over silica (Merck 9385, 50 g) using medium pressure (ca 4 psi) and dichloromethane/methanol (15:1 v/v) as the eluant. The required fractions were combined and the solvent removed in vacuo to give the title compound as a white solid. (0.87 g). 1H NMR (250 MHz, D6 -DMSO) 9.25 (1H, d, J=9 Hz), 5.90 (1H, d, J=3 Hz), 4.79 (1H, d, J=9 Hz), 4.00 (1H, m), 3.71 (3H, s), 3.58 (1H, m), 3.40 (2H, m), 3.16 (1H, m), 2.95 (1H, m), 1.84 (2H, s), 1.57 (2H, m), 1.40 (2H, m), 0.81 (6H, m), Mass analysis: C16H24F3N3O5. 0.5 H2O. Required: C, 47.52; H, 6.23; N, 10.39. Found: C, 47.68; H, 6.05; N, 10.10.

Workup

  1. stirringthe mixture was stirred for 16 hours at 23° C
  2. customThe solvent was removed in vacuo
  3. customthe residue was chromatographed over silica (Merck 9385, 50 g)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3686760eabb94eb5be3f19a3c8c0c9ef
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

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