Triethylamine → HCID 492423, compound

HRID 1603998Notes

Reaction equation

HRID 1603998 reaction equation
[C:1]([NH:4][C@H:5]1[C@H:10]([C:11](=[O:19])[N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[O:9][C:8]([C:20]([O:22]C)=[O:21])=[CH:7][C@H:6]1[N:24]=[N+]=[N-])(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>O1CCCC1.O>[C:1]([NH:4][C@H:5]1[C@H:10]([C:11](=[O:19])[N:12]([CH2:13][CH2:14][CH3:15])[CH2:16][CH2:17][CH3:18])[O:9][C:8]([C:20]([OH:22])=[O:21])=[CH:7][C@H:6]1[NH2:24])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 11776TriphenylphosphineHCID 86754842HCID 86754842, compound

Product 1

HCID 492423HCID 492423, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (4R,5R,6R)-5-acetylamino-4-azido-6-(dipropylcarbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid, methyl ester (500 mg) in tetrahydrofuran (6 ml) under nitrogen was added triphenylphosphine (428 mg). After 3.5 hours at 23° C. water (1 ml) was added adn the solution was stirred for a further 21 hours. Triethylamine (1 ml) was added and stirring was continued for a further 7 hours after which the solvents were removed in vacuo. The resulting liquid was redissolved in ethyl acetate, was dried over anhydrous magnesium sulphate, and the solvent was evaporated in vacuo to leave a yellow solid. The solid was chromatographed over silica (Merck 9385, 45 g) using medium pressure (ca 4 psi) and chloroform/methanol (15:1, v/v) as eluant. Appropriate fractions were combined and the solvent was evaporated in vacuo to afford a white solid which was suspended in water (5 ml) containing triethylamine (2 ml) and was stirred at 50° C. for 1.5 hours. The solvents were removed in vacuo to afford the title compound as a white solid (171 mg). 1H NMR (250MHz, D6 -DMSO) 8.4 (1H, broad s), 5.7 (1H, d, J=1.5Hz), 5.1 (1H, d, J=4Hz), 4.4 (1H, broad s), 3.95 (1H, broad s), 2.95-3.86 (6H, m), 2.0 (3H, s), 1.6 (4H, m), 0.94+0.99 (6H, two t, J=7.5Hz). Mass spec. (low resolution): MH+ =328. Mass analysis: C15H25N3O5. 1.5 H2O Required: C, 50.79; H, 7.90; N, 11.85. Found: C, 50.87; H, 8.04; N, 11.54.

Workup

  1. stirringstirring
  2. waitwas continued for a further 7 hours
  3. customafter which the solvents were removed in vacuo
  4. dissolutionThe resulting liquid was redissolved in ethyl acetate
  5. dry with materialwas dried over anhydrous magnesium sulphate
  6. customthe solvent was evaporated in vacuo
  7. customto leave a yellow solid
  8. customThe solid was chromatographed over silica (Merck 9385, 45 g)
  9. customthe solvent was evaporated in vacuo
  10. customto afford a white solid which
  11. stirringwas stirred at 50° C. for 1.5 hours
  12. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-d4f90b092bef40d1a784de3d2dc6837a
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

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