Mercuric cyanide → HCID 22972450, compound

HRID 1072552Notes

Reaction equation

HRID 1072552 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:77])[CH2:48][C@H:49]([O:61][C:62](=[O:76])[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[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:78]([O:93][C@H:94]([CH2:105][CH2:106][CH2:107][CH2:108][CH2:109][CH2:110][CH2:111][CH2:112][CH2:113][CH2:114][CH3:115])[CH2:95][C:96]([N:98]1[CH2:102][CH2:101][CH2:100][C@H:99]1[CH2:103][OH:104])=[O:97])(=[O:92])[CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH3:91].[Hg](C#N)C#N>ClCCCl.C(Cl)Cl>[C:11]1([O:10][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:33])[Cl:31])=[O:27])[O:22][C@@H:21]([O:104][CH2:103][C@@H:99]3[CH2:100][CH2:101][CH2:102][N:98]3[C:96](=[O:97])[CH2:95][C@H:94]([O:93][C:78](=[O:92])[CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH3:91])[CH2:105][CH2:106][CH2:107][CH2:108][CH2:109][CH2:110][CH2:111][CH2:112][CH2:113][CH2:114][CH3:115])[C@H:20]([NH:37][C:38]([O:40][CH2:41][C:42]([Cl:44])([Cl:45])[Cl:43])=[O:39])[C@H:19]2[O:46][C:47](=[O:77])[CH2:48][C@H:49]([O:61][C:62](=[O:76])[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])([O:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:9])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 11591Mercuric cyanideHCID 22972444HCID 22972444, compoundHCID 68767212HCID 68767212, compound

Product 1

HCID 22972450HCID 22972450, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

(1 a) To a solution of 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl bromide (1.05 g, 0.81 mmol) in dry 1,2-dichloroethane (10 mL) were added 4 Å molecular sieves (0.5 g), anhydrous CaSO4 (2.2 g, 16 mmol), and N-[(R)-3-tetradecanoyloxytetradecanoyl]-(S)-2-pyrrolidinemethanol (0.40 g, 0.75 mmol). The resulting mixture was stirred for 1 h at room temperature, treated with Hg(CN)2 (1.02 g, 4.05 mmol), and heated to reflux for 16 h in the dark. The cooled reaction mixture was diluted with CH2Cl2 and filtered. The filtrate was washed with 1 N aq KI, dried (Na2SO4), and concentrated. Flash chromatography on silica gel (gradient elution, 15→20% EtOAc/hexanes) afforded 0.605 g (43%) of N-[(R)-3-tetradecanoyloxytetradecanoyl]-(S)-2-pyrrolidinylmethyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside as an amorphous solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 h in the dark
  3. customThe cooled reaction mixture
  4. filtrationfiltered
  5. washThe filtrate was washed with 1 N aq KI
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6ccbf7908ef54aa69853f6253d8a7f96
Source dataset
uspto-grants-2005_06
Patent number
US06911434B2

Reaction notes

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