Acetone → HCID 86620109, compound

HRID 1644788Notes

Reaction equation

HRID 1644788 reaction equation
C([O:8][C@@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([CH3:31])[O:11][C@H:10]1[O:32][C@@H:33]1[C@@H:42]([O:43][C@H:44]2[O:73][C@H:72]([CH2:74][O:75][CH2:76][C:77]3[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=3)[C@@H:63]([O:64][CH2:65][C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)[C@H:54]([O:55][CH2:56][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[C@H:45]2[O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@H:41]([CH3:83])[O:40][C@@H:35]([O:36][CH2:37][CH:38]=[CH2:39])[C@@H:34]1[O:84][C:85](=[O:92])[C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)(=O)CCC(C)=O.NN.CC(C)=O>N1C=CC=CC=1.C(O)(=O)C>[CH2:16]([O:15][C@@H:14]1[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([CH3:31])[O:11][C@@H:10]([O:32][C@@H:33]2[C@@H:42]([O:43][C@H:44]3[O:73][C@H:72]([CH2:74][O:75][CH2:76][C:77]4[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=4)[C@@H:63]([O:64][CH2:65][C:66]4[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=4)[C@H:54]([O:55][CH2:56][C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)[C@H:45]3[O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C@H:41]([CH3:83])[O:40][C@@H:35]([O:36][CH2:37][CH:38]=[CH2:39])[C@@H:34]2[O:84][C:85](=[O:92])[C:86]2[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=2)[C@@H:9]1[OH:8])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 9321HydrazineHCID 86620110HCID 86620110, compound

Product 1

HCID 86620109HCID 86620109, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1049PyridineSolvent

Procedure

The trisaccharide 215 (200 mg, 0.16 mmol) was treated with 0.4 mL of a solution 1 M of hydrazine (100 mg) diluted in a mixture of pyridine (1.6 mL) and acetic acid (0.4 mL) at rt. The solution was stirred during 20 min. Acetone (1.2 mL) was added and the solution was concentrated. The residue was eluted from a column of silica gel with 98.5:1.5 DCM-EtOAc to give 216 (174 mg) as a foam. Although, contaminated with hydrazine salts, the 1H NMR spectrum showed that compound 216 had NMR data identical to that of a reference compound. (F. Bélot, K. Wright, C. Costachel, A. Phalipon, L. A. Mulard, J. Org. Chem. 2004, 69, 1060-1074)

Workup

  1. concentrationthe solution was concentrated
  2. washThe residue was eluted from a column of silica gel with 98.5:1.5 DCM-EtOAc

Sources & evidence

ORD record
ord-26846d6f12d54a84a034bb519e2a75ad
Source dataset
uspto-grants-2012_02
Patent number
US08124380B2

Reaction notes

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