Mercuric cyanide → HCID 22972446, compound

HRID 1170889Notes

Reaction equation

HRID 1170889 reaction equation
[C:1]1([O:7][P:8]([O:17][C@@H:18]2[C@@H:23]([CH2:24][O:25][C:26]([O:28][C:29]([CH3:35])([CH3:34])[C:30]([Cl:33])([Cl:32])[Cl:31])=[O:27])[O:22][C@H:21](Br)[C@H:20]([NH:37][C:38]([O:40][CH2:41][C:42]([Cl:45])([Cl:44])[Cl:43])=[O:39])[C@H:19]2[O:46][C:47](=[O:73])[CH2:48][C@H:49]([O:61][C:62](=[O:72])[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:74]([O:85][C@H:86]([CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH2:104][CH2:105][CH2:106][CH3:107])[CH2:87][C:88]([N:90]1[CH2:94][CH2:93][CH2:92][C@H:91]1[CH2:95][OH:96])=[O:89])(=[O:84])[CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83].[Hg](C#N)C#N>ClCCCl.C(Cl)Cl>[C:1]1([O:7][P:8]([O:17][C@@H:18]2[C@@H:23]([CH2:24][O:25][C:26]([O:28][C:29]([CH3:34])([CH3:35])[C:30]([Cl:32])([Cl:31])[Cl:33])=[O:27])[O:22][C@@H:21]([O:96][CH2:95][C@@H:91]3[CH2:92][CH2:93][CH2:94][N:90]3[C:88](=[O:89])[CH2:87][C@H:86]([O:85][C:74](=[O:84])[CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83])[CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH2:104][CH2:105][CH2:106][CH3:107])[C@H:20]([NH:37][C:38]([O:40][CH2:41][C:42]([Cl:43])([Cl:44])[Cl:45])=[O:39])[C@H:19]2[O:46][C:47](=[O:73])[CH2:48][C@H:49]([O:61][C:62](=[O:72])[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])([O:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11591Mercuric cyanideHCID 22972443HCID 22972443, compoundHCID 68768205HCID 68768205, compound

Product 1

HCID 22972446HCID 22972446, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-decanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide (1.70 g, 1.38 mmol) in dry 1,2-dichloroethane (3.5 mL) were added 4 Å molecular sieves (0.6 g), anhydrous CaSO4 (1.2 g, 8.8 mmol), and N-[(R)-3-decanoyloxytetradecanoyl]-(S)-2-pyrrolidinemethanol (0.60 g, 1.24 mmol). The resulting mixture was stirred for 1 h at room temperature, treated with Hg(CN)2 (0.63 g, 2.5 mmol), and heated to reflux for 6 h in the dark. The cooled reaction mixture was diluted with CH2Cl2 and filtered through a bed of celite. The filtrate was washed with 1 N aq KI, dried (Na2SO4), and concentrated. Flash chromatography on silica gel (gradient elution, 25→40% EtOAc/hexanes) afforded 1.82 g (80%) of N-[(R)-3-decanoyloxytetradecanoyl]-(S)-2-pyrrolidinylmethyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-decanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside as a colorless oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 h in the dark
  3. customThe cooled reaction mixture
  4. filtrationfiltered through a bed of celite
  5. washThe filtrate was washed with 1 N aq KI
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-484c0e7816664150ba54c297c1b9870f
Source dataset
uspto-grants-2010_11
Patent number
US07829542B2

Reaction notes

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