N-Methylaniline → (2R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((6R,7S,8R,8aS)-7-acetamido-2-phenyl-8-(2-(tritylthio)acetoxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yloxy)propanoic acid

HRID 2410212Notes

Reaction equation

HRID 2410212 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([CH2:26][O:27][C@@H:28]3[O:37][CH:36]4[C@@H:31]([O:32][CH:33]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[O:34][CH2:35]4)[C@H:30]([O:44][C:45](=[O:67])[CH2:46][S:47][C:48]([C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)[C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[C@@H:29]3[NH:68][C:69](=[O:71])[CH3:70])[C:20]([O:22]CC=C)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CNC1C=CC=CC=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([CH2:26][O:27][C@@H:28]3[O:37][CH:36]4[C@@H:31]([O:32][CH:33]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[O:34][CH2:35]4)[C@H:30]([O:44][C:45](=[O:67])[CH2:46][S:47][C:48]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)([C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=4)[C:61]4[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=4)[C@@H:29]3[NH:68][C:69](=[O:71])[CH3:70])[C:20]([OH:22])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 7515N-MethylanilineHCID 86651901(2R)-allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((6R,7S,8R,8aS)-7-acetamido-2-phenyl-8-(2-(tritylthio)acetoxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yloxy)propanoate

Product 1

HCID 86651903(2R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((6R,7S,8R,8aS)-7-acetamido-2-phenyl-8-(2-(tritylthio)acetoxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yloxy)propanoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Allyl protected glycosyl amino acid 34 (135 mg, 0.14 mmol) was suspended in THF (6 ml). N-methylaniline (0.15 ml, 1.38 mmol) and Pd(PPh3)4 (16 mg, 0.01 mmol) were added and the reaction stirred at rt for 20 min. The solvent was removed in vacuo and the product purified by column chromatography (eluent: 95:5 v/v dichloromethane/methanol—9:1 v/v dichloromethane/methanol) to give the desired acid 35 as a pale yellow solid (123 mg, 95%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe product purified by column chromatography (eluent: 95:5 v/v dichloromethane/methanol—9:1 v/v dichloromethane/methanol)

Sources & evidence

ORD record
ord-381569df18ee4b8f87eea61e60c50b0c
Source dataset
uspto-grants-2014_08
Patent number
US08816050B2

Reaction notes

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