Ammonia → HCID 13278999, compound

HRID 1388298Notes

Reaction equation

HRID 1388298 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15][C@H:16]2[O:33][C@H:32]([CH2:34][O:35]C(=O)C)[C@@H:27]([O:28]C(=O)C)[C@H:22]([O:23]C(=O)C)[C@H:17]2[O:18]C(=O)C)[C@@H:8]([CH2:39][O:40]C(=O)C)[O:7][C@H:6]1[S:44][C:45]1[CH:50]=[CH:49][C:48]([NH:51][C:52]([NH:54][C:55]2[CH:60]=[CH:59][C:58]([S:61][C@@H:62]3[O:99][C@H:98]([CH2:100][O:101]C(=O)C)[C@@H:73]([O:74][C@H:75]4[O:92][C@H:91]([CH2:93][O:94]C(=O)C)[C@@H:86]([O:87]C(=O)C)[C@H:81]([O:82]C(=O)C)[C@H:76]4[O:77]C(=O)C)[C@H:68]([O:69]C(=O)C)[C@H:63]3[O:64]C(=O)C)=[CH:57][CH:56]=2)=[O:53])=[CH:47][CH:46]=1)(=O)C.N>CO>[C@H:75]1([O:74][C@@H:73]2[C@@H:98]([CH2:100][OH:101])[O:99][C@@H:62]([S:61][C:58]3[CH:57]=[CH:56][C:55]([NH:54][C:52]([NH:51][C:48]4[CH:47]=[CH:46][C:45]([S:44][C@@H:6]5[O:7][C@H:8]([CH2:39][OH:40])[C@@H:9]([O:15][C@H:16]6[O:33][C@H:32]([CH2:34][OH:35])[C@@H:27]([OH:28])[C@H:22]([OH:23])[C@H:17]6[OH:18])[C@H:10]([OH:11])[C@H:5]5[OH:4])=[CH:50][CH:49]=4)=[O:53])=[CH:60][CH:59]=3)[C@H:63]([OH:64])[C@H:68]2[OH:69])[O:92][C@H:91]([CH2:93][OH:94])[C@@H:86]([OH:87])[C@H:81]([OH:82])[C@H:76]1[OH:77]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13278997HCID 13278997, compound

Product 1

HCID 13278999HCID 13278999, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 17.3 g of N,N'-bis[4-[[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]urea in 500 ml of methanol saturated with ammonia was stirred in an ice bath for 6 hours and then refrigerated overnight. The mixture was filtered through a sintered glass funnel and concentrated in vacuo to a foam. The foam was triturated with ethanol, filtered, washed with ethanol then ether and dried, giving 11.42 g of the desired intermediate.

Workup

  1. customrefrigerated overnight
  2. filtrationThe mixture was filtered through a sintered glass funnel
  3. concentrationconcentrated in vacuo to a foam
  4. customThe foam was triturated with ethanol
  5. filtrationfiltered
  6. washwashed with ethanol
  7. dry with materialether and dried

Sources & evidence

ORD record
ord-cda0e2342f1445a38a856f9670396b57
Source dataset
uspto-grants-1984_02
Patent number
US04431636

Reaction notes

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