Diisopropylethylamine → HCID 57128419, compound

HRID 1604003Notes

Reaction equation

HRID 1604003 reaction equation
[C:1]([NH:4][C@H:5]1[C@@H:10]([O:11][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=[C:8]([C:29]([O:31]C)=[O:30])[O:7][C@H:6]1[C:33]([O-:35])=O)(=[O:3])[CH3:2].Cl.[C:37]1([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][NH:45][CH2:46][CH2:47][CH3:48])=[CH:39][CH:38]=1.C(N(C(C)C)CC)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[C:1]([NH:4][C@H:5]1[C@H:6]([C:33](=[O:35])[N:45]([CH2:44][CH2:43][C:40]2[CH:39]=[CH:38][C:37]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)=[CH:42][CH:41]=2)[CH2:46][CH2:47][CH3:48])[O:7][C:8]([C:29]([OH:31])=[O:30])=[CH:9][C@@H:10]1[OH:11])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 70198874HCID 70198874, compoundHCID 86754847HCID 86754847, compound

Product 1

HCID 57128419HCID 57128419, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (2R,3R,4S)-3-acetylamino-4-(tert-butyldiphenylsilanyloxy)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid, 6-methyl ester (2.0 g), (2-biphenyl-4-yl-ethyl)propylamine hydrochloride (1.33 g) and diisopropyl ethylamine (2.52 ml) in anhydrous dimethylformamide (5 ml) was added 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl-uronium tetrafluoroborate (1.55 g). The reaction was stirred at 23° C. for 24 hours then diluted with ethyl acetate (200 ml) and washed with water (2×200 ml), dilute hydrochloric acid (100 ml), saturated sodium bicarbonate solution (100 ml) and brine (100 ml). The organic phase was dried over anhydrous magnesium sulphate and the solvent was removed in vacuo and the residue was chromatographed over silica (Merck 9385, 20 g) using medium pressure (ca 4 psi) and cyclohexane/ethyl acetate (10:1 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 (1.6 g). 1H NMR (250 MHz, D6 -DMSO rotamers) 8.16+8.12 (1H,2×d, J=10 Hz), 7.64 (8H, m), 7.53-7.30 (11H, m), 5.50 (1H, m), 5.11 (1H, m), 4.54+4.40 (1H, 2×m), 4.26 (1H, m), 3.71+3.65 (3H, 2×s), 3.6-3.1 (4H, m), 2.92 (1H, m), 2.82 (1H, m), 1.81+1.79 (3H, 2×s), 1.62 (1H, m), 1.52 (1H, m), 1.02 (9H, s), 0.91+0.82 (3H, 2×t, J=7 Hz). Mass analysis: C43H50N2O6Si. Required: C, 71.84; H, 7.01; N, 3.90. Found: C, 71.54; H, 7.33; N, 3.88.

Workup

  1. washwashed with water (2×200 ml), dilute hydrochloric acid (100 ml), saturated sodium bicarbonate solution (100 ml) and brine (100 ml)
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  3. customthe solvent was removed in vacuo
  4. customthe residue was chromatographed over silica (Merck 9385, 20 g)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ef4d00f7018f409da5c2fb5cc84de4ff
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

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