Pyridine → HCID 10676004, compound

HRID 1603991Notes

Reaction equation

HRID 1603991 reaction equation
[CH:1]([O:14][C:15]([C:17]1[O:22][C@@H:21]([C:23]([OH:25])=[O:24])[C@H:20]([NH:26][C:27](=[O:29])[CH3:28])[C@@H:19]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:18]=1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.FC(F)(F)C(O[C:49]1[C:54]([F:55])=[C:53]([F:56])[C:52]([F:57])=[C:51]([F:58])[C:50]=1[F:59])=O>CN(C)C=O.C(OCC)(=O)C>[F:55][C:54]1[C:53]([F:56])=[C:52]([F:57])[C:51]([F:58])=[C:50]([F:59])[C:49]=1[O:24][C:23]([C@H:21]1[C@H:20]([NH:26][C:27](=[O:29])[CH3:28])[C@@H:19]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:18]=[C:17]([C:15]([O:14][CH:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:16])[O:22]1)=[O:25]

Participants

6

Reactant 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 10553734HCID 10553734, compound

Product 1

HCID 10676004HCID 10676004, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2R,3R,4S)-3-Acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester (3.36 g) was dissolved in dry dimethylformamide (10 ml) and pyridine (0.632 g) under nitrogen and stirred at 23° C. To this was added pentafluorophenyl trifluoroacetate (2.02 g). After 3 hours the reaction mixture was diluted with ethyl acetate (250 ml) and washed with dilute hydrochloric acid (3×50 ml), dilute sodium bicarbonate solution (3×50 ml) and brine (50 ml). The organic phase was dried over anhydrous magnesium sulphate and the solvent was removed in vacuo to give the title compound as an off-white foam. (4.353 g); 1H NMR (250 MHz, DMSO) 8.22 (1H, d, J=8Hz), 7.50-7.27 (10H, m), 7.06 (1H, m), 6.94 (1H, s), 6.18 (1H, d, J=3.8Hz), 5.25 (1H, d, J=6.8Hz), 4.42 (1H, m), 4.29 (1H, m), 1.82 (3H, s), 1.38 (9H, s).

Workup

  1. washwashed with dilute hydrochloric acid (3×50 ml), dilute sodium bicarbonate solution (3×50 ml) and brine (50 ml)
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4c2f94859ca648b18bdb3801e1bf010e
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

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