Dichloromethane → 4-[9-(N-t-butyloxycarbonyl-N-4,4,5,5,5-pentafluoropentylaminosulfonylamino)nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

HRID 1792312Notes

Reaction equation

HRID 1792312 reaction equation
C(OC([NH:8][S:9]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]1[C:31]2[C:26](=[CH:27][C:28]([O:32][CH2:33][O:34][CH3:35])=[CH:29][CH:30]=2)[O:25][CH2:24][C:23]1([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][O:45][CH3:46])=[CH:39][CH:38]=1)[CH3:36])(=[O:11])=[O:10])=O)(C)(C)C.[F:47][C:48]([F:57])([C:53]([F:56])([F:55])[F:54])[CH2:49][CH2:50][CH2:51]O.C1(P([C:71]2[CH:76]=[CH:75]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=N[C:79]([O:81]CC)=[O:80].Cl[CH2:90]Cl>C(OCC)(=O)C.CCCCCC>[C:76]([O:81][C:79]([N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]1[C:31]2[C:26](=[CH:27][C:28]([O:32][CH2:33][O:34][CH3:35])=[CH:29][CH:30]=2)[O:25][CH2:24][C:23]1([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][O:45][CH3:46])=[CH:39][CH:38]=1)[CH3:36])[S:9]([NH:8][CH2:51][CH2:50][CH2:49][C:48]([F:57])([F:47])[C:53]([F:56])([F:55])[F:54])(=[O:10])=[O:11])=[O:80])([CH3:75])([CH3:71])[CH3:90]

Participants

8

Reactant 5

HCID 6344Dichloromethane2×HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5479674,4,5,5,5-Pentafluoropentan-1-olHCID 220334184-[9-(N-t-butyloxycarbonylaminosulfonylamino)nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

Product 1

HCID 572515044-[9-(N-t-butyloxycarbonyl-N-4,4,5,5,5-pentafluoropentylaminosulfonylamino)nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchromanYield 67%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[9-(N-t-butyloxycarbonylaminosulfonylamino)nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (5 7 mg, 0.088 mmol) in dichloromethane (2 ml) were added 4,4,5,5,5-pentafluoropentyl alcohol (15.6 mg, 0.088 mmol) and triphenylphosphine (23 mg, 0.088 mmol) at room temperature. Diethyl azodicarboxylate in dichloromethane (1 ml) was added dropwise to the reaction mixture at the same temperature until the color of the reaction solution turned to yellow, which was then stirred overnight. After the reaction was completed, the organic solvent was evaporated under reduced pressure. The crude product thus obtained was subjected to preparative TLC (n-hexane:ethyl acetate=8:2) to give the title compound (47 mg, yield 67%) as a white solid.

Workup

  1. customthe organic solvent was evaporated under reduced pressure
  2. customThe crude product thus obtained

Sources & evidence

ORD record
ord-93bee10c868143f38eb6769bca14ba9a
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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