Ammonium Chloride → HCID 86601372, compound

HRID 346855Notes

Reaction equation

HRID 346855 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:14][N:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:21][CH:22]=2)[CH2:17][CH:16]1[CH3:34].C1CCN2C(=NCCC2)CC1.[CH3:46][O:47][C:48](=[O:51])[CH2:49]Br.[NH4+].[Cl-]>CN(C=O)C.CCOCC>[CH3:46][O:47][C:48](=[O:51])[CH2:49][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[O:6][C:2]([CH3:1])=[C:3]([CH2:14][N:15]3[C:23]4[C:18](=[CH:19][C:20]([C:24]([OH:33])([C:25]([F:26])([F:27])[F:28])[C:29]([F:32])([F:31])[F:30])=[CH:21][CH:22]=4)[CH2:17][CH:16]3[CH3:34])[N:4]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 135848758HCID 135848758, compound

Product 1

HCID 86601372HCID 86601372, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 40 mg (0.083 mmol) of 4-{5-methyl-4-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-ylmethyl]-oxazol-2-yl}-phenol (example 99) in 0.5 mL of DMF was treated with 0.01 mL of DBU and 0.01 mL (0.1 mmol) of methylbromoacetate. The mixture was stirred overnight at RT and distributed between Et2O and a saturated aqueous solution of NH4Cl. Drying of the combined organic phases, evaporation of the solvent and chromatography on silica gel with n-heptane/EtOAc 1:1 gave (4-{5-methyl-4-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-ylmethyl]-oxazol-2-yl}-phenoxy)-acetic acid methyl ester, off-white foam, MS: 559 (MH+).

Workup

  1. dry with materialDrying of the combined organic phases, evaporation of the solvent and chromatography on silica gel with n-heptane/EtOAc 1:1

Sources & evidence

ORD record
ord-9c0e37c74d004cd29c1b34a39c898d80
Source dataset
uspto-grants-2007_02
Patent number
US07173048B2

Reaction notes

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