Triphenylphosphine → HCID 86672799, compound

HRID 1755123Notes

Reaction equation

HRID 1755123 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[C:11]2([CH2:18][CH2:17][N:16]([S:19]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:26][C:25]=3[CH3:37])(=[O:21])=[O:20])[CH2:15][CH2:14]2)[N:10]=[C:9]1[C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([OH:48])[CH:39]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:49]([O:53][C:54](=[O:66])[N:55]([CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64]O)[CH3:56])([CH3:52])([CH3:51])[CH3:50].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C(/N=N/C(N(C)C)=O)=O)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[C:11]2([CH2:18][CH2:17][N:16]([S:19]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])=[CH:26][C:25]=3[CH3:37])(=[O:21])=[O:20])[CH2:15][CH2:14]2)[N:10]=[C:9]1[C:38]1[CH:43]=[C:42]([C:44]([F:46])([F:47])[F:45])[CH:41]=[C:40]([O:48][CH2:64][CH2:63][O:62][CH2:61][CH2:60][O:59][CH2:58][CH2:57][N:55]([C:54]([O:53][C:49]([CH3:50])([CH3:52])[CH3:51])=[O:66])[CH3:56])[CH:39]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5353800DiamideHCID 66818057HCID 66818057, compoundHCID 86672798HCID 86672798, compound

Product 1

HCID 86672799HCID 86672799, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

8-[2-(4-tert-Butoxycarbonyl-2-methyl-phenyl)-ethanesulfonyl]-2-(3-hydroxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-3-carboxylic acid tert-butyl ester (30.0 mg, 43.1 μmol), {2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethyl}-methyl-carbamic acid tert-butyl ester (22.7 mg, 86.2 μmol) and triphenylphosphine (22.6 mg, 86.2 μmol) were dissolved in THF (0.22 mL). TMAD (14.8 mg, 86.2 μmol) was added and the mixture was stirred at 60° C. for 30 minutes in a nitrogen atmosphere. The reaction solution was concentrated under reduced pressure, and the resulting residue was then purified by silica gel column chromatography (hexane-ethyl acetate) to give 2-[3-(2-{2-[2-(tert-butoxycarbonyl-methyl-amino)-ethoxy]-ethoxy}-ethoxy)-5-trifluoromethyl-phenyl]-8-[2-(4-tert-butoxycarbonyl-2-methyl-phenyl)-ethanesulfonyl]-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-3-carboxylic acid tert-butyl ester (37.4 mg, 86%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was then purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-375599880bcf41f6bc57cb21d132b6b7
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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