Ethyl Acetate → HCID 178475055, compound

HRID 1603995Notes

Reaction equation

HRID 1603995 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]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[N:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[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.FC(F)(F)C(O[C:53]1[C:58]([F:59])=[C:57]([F:60])[C:56]([F:61])=[C:55]([F:62])[C:54]=1[F:63])=O.C(OCC)(=O)C>CN(C)C=O.N1C=CC=CC=1>[F:59][C:58]1[C:57]([F:60])=[C:56]([F:61])[C:55]([F:62])=[C:54]([F:63])[C:53]=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]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[N:32][C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[CH:18]=[C:17]([C:15]([O:14][CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:16])[O:22]1)=[O:25]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 178475054HCID 178475054, compound

Product 1

HCID 178475055HCID 178475055, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (2R,3R,4S)-3-Acetylamino-4-[2,3-bis(tert-butoxycarbonyl)-guanidino]-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester (4.4 g) in dry dimethylformamide (10 ml) and pyridine (0.70 ml) was added pentafluorophenyl trifuoroacetate (1.27 ml) and the reaction was stirred at 23° C. for 1 hour. More pyridine (0.70 ml) and pentafluorophenyl trifluoroacetate (1.27 ml) was added and the reaction was stirred for a further 2 hours. The reaction mixture was diluted using ethyl acetate and washed consecutively using 1N hydrochloric acid, saturated sodium bicarbonate solution and brine. The organic phase was dired over anhydrous magnesium sulphate and the solvent was removed in vacuo to give the crude title compound as a tan foam, (8.11 g); 1H NMR (250MHz, D6 -DMSO) 9.97 (1H, broad s), 7.49--7.27 (11H, m), 6.91 (1H, s), 6.52 (1H, m), 4.93 (1H, m), 4.58 (1H, m), 4.47 (1H, m), 1.88 (3H,s), 1.42 (18H, s).

Workup

  1. stirringthe reaction was stirred for a further 2 hours
  2. additionThe reaction mixture was diluted
  3. washwashed consecutively
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-80eff3dec8c04a0a8923af54083ce754
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

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