Trityl chloride → HCID 136602507, compound

HRID 870285Notes

Reaction equation

HRID 870285 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:12][CH2:13][C@@H:14]1[CH2:19][NH:18][CH2:17][C@H:16]([N:20]2[CH:28]=[N:27][C:26]3[C:25](=[O:29])[NH:24][C:23]([NH:30][C:31](=[O:40])[CH2:32][O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[N:22][C:21]2=3)[O:15]1.C(N(CC)CC)C.[C:48](Cl)([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>ClCCl>[OH:12][CH2:13][C@@H:14]1[CH2:19][N:18]([C:48]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)([C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH2:17][C@H:16]([N:20]2[CH:28]=[N:27][C:26]3[C:25](=[O:29])[NH:24][C:23]([NH:30][C:31](=[O:40])[CH2:32][O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[N:22][C:21]2=3)[O:15]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 137187590HCID 137187590, compound

Product 1

HCID 136602507HCID 136602507, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 30 mL of dichloromethane was suspended 2.0 g of N9-{(2R,6S)-6-(hydroxymethyl)morpholin-2-yl}-N2-(phenoxyacetyl)guanine p-toluenesulfonate (REFERENCE EXAMPLE 1), and 13.9 g of triethylamine and 18.3 g of trityl chloride were added to the suspension under ice cooling. The mixture was stirred at room temperature for an hour. The reaction solution was washed with saturated sodium bicarbonate aqueous solution and then with, water, and dried over sodium sulfate. The organic layer was concentrated under reduced pressure. To the residue was added 40 mL of 0.2 M sodium citrate buffer (pH 3)/methanol (1:4 (v/v)), and the mixture was stirred. Subsequently, 40 mL of water was added and the suspension mixture was stirred for an hour under ice cooling. The precipitates were taken out by filtration, washed with cold methanol and dried to give 1.84 g of the objective compound (yield: 82.0%).

Workup

  1. additionwere added to the suspension under ice cooling
  2. washThe reaction solution was washed with saturated sodium bicarbonate aqueous solution
  3. dry with materialwith, water, and dried over sodium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. additionTo the residue was added 40 mL of 0.2 M sodium citrate buffer (pH 3)/methanol (1:4 (v/v))
  6. stirringthe mixture was stirred
  7. additionSubsequently, 40 mL of water was added
  8. stirringthe suspension mixture was stirred for an hour under ice cooling
  9. filtrationThe precipitates were taken out by filtration
  10. washwashed with cold methanol
  11. customdried

Sources & evidence

ORD record
ord-4bec0621d6404fbcabc88097c9b4edb6
Source dataset
uspto-grants-2015_03
Patent number
US08969551B2

Reaction notes

Loading…