HCID 178496437, compound → HCID 178496438, compound

HRID 1828092Notes

Reaction equation

HRID 1828092 reaction equation
[CH2:1]([O:8][C:9](=[O:43])/[N:10]=[C:11](/[NH2:42])\[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20](=[O:41])[CH:21]([O:39][CH3:40])[C:22]2[N:26](COCC[Si](C)(C)C)[C:25]3[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=3[N:23]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl>[CH2:1]([O:8][C:9](=[O:43])/[N:10]=[C:11](/[NH2:42])\[C:12]1[CH:13]=[CH:14][C:15]([CH2:18][NH:19][C:20](=[O:41])[CH:21]([C:22]2[NH:23][C:24]3[CH:38]=[CH:37][CH:36]=[CH:35][C:25]=3[N:26]=2)[O:39][CH3:40])=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 178496437HCID 178496437, compound

Product 1

HCID 178496438HCID 178496438, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(RS)-[1-Amino-1-[4-({2-methoxy-2-[l -(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-acetylamino }-methyl)-phenyl]-meth-(E)-ylidene]-carbamic acid benzyl ester (0.5 g) was heated in 5 N HCl (20 ml) to 50° C. and stirring at that temperature was continued for 4 h. After cooling to r.t., the mixture was washed with EtOAc and cooled to 0° C. The pH was brought to ˜12 by the dropwise addition of 4 N NaOH. The mixture was then extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), filtered and concentrated to give (RS)-[1-amino-1-(4-{[2-(1H-benzoimidazol-2-yl)-2-methoxy-acetylamino]-methyl}-phenyl)-meth-(E)-ylidene]-carbamic acid benzyl ester (0.258 g) as light yellow solid. MS472.3 ([M+H]+)

Workup

  1. washthe mixture was washed with EtOAc
  2. temperaturecooled to 0° C
  3. additionThe pH was brought to ˜12 by the dropwise addition of 4 N NaOH
  4. extractionThe mixture was then extracted with EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-55aae54022074ee7903c8cd28ec35b3e
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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