Tetrabutylammonium Fluoride → tert-Butyl (3-{cyclopropyl[3-hydroxy-5-(3-methoxypropyl)benzyl](cyclopropyl)amino}-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate

HRID 561870Notes

Reaction equation

HRID 561870 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]([CH:49]=[C:50]([CH2:52][CH2:53][CH2:54][O:55][CH3:56])[CH:51]=1)[CH2:12][N:13]([CH:46]1[CH2:48][CH2:47]1)[C:14](=[O:45])[CH:15]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][O:35][C:36]2[C:41]([Cl:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:37]=2[Cl:44])=[CH:28][CH:27]=1)[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(C(C)(C)C)(C)C.[F-].C([N+](C[CH2:72][CH2:73][CH3:74])(CCCC)CCCC)CCC>C1COCC1>[CH:72]1([C:46]2([N:13]([CH2:12][C:11]3[CH:49]=[C:50]([CH2:52][CH2:53][CH2:54][O:55][CH3:56])[CH:51]=[C:9]([OH:8])[CH:10]=3)[C:14](=[O:45])[CH:15]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][O:35][C:36]4[C:41]([Cl:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:37]=4[Cl:44])=[CH:28][CH:27]=3)[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:47][CH2:48]2)[CH2:73][CH2:74]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86635934Tert-butyl (3-[[3-{[tert-butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzyl] (cyclopropyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate

Product 1

HCID 86635933tert-Butyl (3-{cyclopropyl[3-hydroxy-5-(3-methoxypropyl)benzyl](cyclopropyl)amino}-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (3-[[3-{[tert-butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzyl] (cyclopropyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate from the previous step (1 eq.) in THF (0.05 M) was added tetrabutylammonium fluoride (1.0 M THF solution, 1.5 eq.). The resulting golden yellow solution was stirred at RT for 8 h. The reaction mixture was quenched with sat. aq. NH4Cl and then extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 2:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc) afforded the title compound as a white semisolid.

Workup

  1. customThe reaction mixture was quenched with sat. aq. NH4Cl
  2. extractionextracted with ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 2:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-a260e3c108e843e6857cd2e0c25c1e1a
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

Loading…