Methanol → HCID 178426695, compound

HRID 1866846Notes

Reaction equation

HRID 1866846 reaction equation
C(OC(=O)[NH:7][CH:8]([C:21](=[O:47])[N:22]([CH:26]([C:36]1[NH:37][CH:38]=[C:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:40]=1)[CH2:27][O:28]CC1C=CC=CC=1)[CH:23]([CH3:25])[CH3:24])[CH2:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17](=[O:19])[NH2:18])=[CH:12][C:11]=1[CH3:20])(C)(C)C.I[Si](C)(C)C.CO.O.C(#N)C>C(Cl)(Cl)Cl>[NH2:7][CH:8]([C:21](=[O:47])[N:22]([CH:26]([C:36]1[NH:37][CH:38]=[C:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:40]=1)[CH2:27][OH:28])[CH:23]([CH3:25])[CH3:24])[CH2:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]([NH2:18])=[O:19])=[CH:12][C:11]=1[CH3:20]

Participants

6

Reactant 4

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 18373917Acetonitrile--water (1/1)HCID 178426698HCID 178426698, compound

Product 1

HCID 178426695HCID 178426695, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of [1-{[2-benzyloxy-1-(4-phenyl-1H-imidazol-2-yl)-ethyl]-isopropyl-carbamoyl}-2-(4-carbamoyl-2,6-dimethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester, (0.287 g, 0.439 mmol), in chloroform (10 mL) was cooled in an ice bath and treated with 0.62 mL (4.4 mmol) of iodotrimethylsilane. The reaction, which immediately clouded, was warmed slowly to room temperature while stirring. After 16 h, the reaction was cooled in an ice bath to 5-10° C. and treated with 100 mL of MeOH. The quenched mixture was stirred at 5-10° C. for 30 min, removed from the ice bath and stirred for an additional 30 min, and concentrated in vacuo to yield an orange residue that was subjected to reverse phase HPLC (water/acetonitrile/0.1% TFA). The fractions of interest were combined and the sample was lyophilized to yield 4-(2-amino-2-{[2-hydroxy-1-(4-phenyl-1H-imidazol-2-yl)-ethyl]-isopropyl-carbamoyl}-ethyl)-3,5-dimethyl-benzamide (TFA salt) as a white powder (HPLC: 99% @ 254 nm and 100% @ 214 nm)

Workup

  1. customThe reaction, which
  2. temperaturethe reaction was cooled in an ice bath to 5-10° C.
  3. stirringThe quenched mixture was stirred at 5-10° C. for 30 min
  4. customremoved from the ice bath
  5. stirringstirred for an additional 30 min
  6. concentrationconcentrated in vacuo
  7. customto yield an orange residue that

Sources & evidence

ORD record
ord-b0612a548c5b4792a201caff7724dbe5
Source dataset
uspto-grants-2009_12
Patent number
US07629488B2

Reaction notes

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