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

HRID 1604001Notes

Reaction equation

HRID 1604001 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[OH:29])(=[O:3])[CH3:2].C(N(CC)CC)C>C(N(CC)CC)C.O>[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]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86754845(4R,5R,6R)-5-Acetylamino-4-hydroxy-6-(phenethylpropylcarbamoyl)-5,6-dihydro-4-H-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 53.5%

Reagents, catalysts & solvents 1

HCID 12210273Ethanamine, N,N-diethyl-, monohydrateSolvent

Procedure

(4R,5R,6R)-5-Acetylamino-4-hydroxy-6-(phenethylpropylcarbamoyl)-5,6-dihydro-4-H-pyran-2-carboxylic acid, methyl ester (300 mg) in triethylamine/water (1:2, 1.5 ml) was heated at 50° C. for 2 hours. Further triethylamine (1 ml) was added and the reaction heated for 2 hours. The reaction mixture was evaporated to dryness and co-evaporated with toluene (5 ml, ×3) and ether and dried to give the title compound (155 mg). 1H NMR (250MHz, D6 -DMSO, rotamers) 7.7 (1H, 2×d, J=9Hz), 7.2--7.4 (5H, m), 5.8 (1H, 2×d, J=5Hz), 4.8 (1H, 2×d, J=8Hz)), 4.2 (1H, m), 4.1 (1H, m), 3.0-3.8 (5H, m), 2.7--2.9 (2H, m) 1.8 (3H, two s) 1.4-1.6 (2H, m) 0.8 (3H, m). Mass Spec. (Low resolution): MH+ =391. Mass Analysis: C20H26N2O6.0.8 C6H5N, 1.0 H2O Requires: C, 60.9; H,8.2; N, 8.0. Found: C, 60.9; H, 8.0; N, 8.1.

Workup

  1. temperaturethe reaction heated for 2 hours
  2. customThe reaction mixture was evaporated to dryness and co-evaporated with toluene (5 ml, ×3) and ether
  3. customdried

Sources & evidence

ORD record
ord-0503615d35024dc8974878bec3ebd7f5
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

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