Chlorotrimethylsilane → [(1S)-1-(4-methoxycarbonylphenyl)ethyl]azanium chloride

HRID 870034Notes

Reaction equation

HRID 870034 reaction equation
C(OC([NH:8][C@H:9]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.[Cl:20][Si](C)(C)[CH3:22]>CO>[Cl-:20].[CH3:22][O:17][C:15]([C:14]1[CH:18]=[CH:19][C:11]([C@@H:9]([NH3+:8])[CH3:10])=[CH:12][CH:13]=1)=[O:16]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 51358474(S)-4-(1-Boc-amino-ethyl)-benzoic acid

Product 1

HCID 161770108[(1S)-1-(4-methoxycarbonylphenyl)ethyl]azanium chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}benzoic acid from Example 1, Step 8 (48.0 g, 181 mmol) in MeOH (175 mL) at r.t. was added chlorotrimethylsilane (116 mL, 905 mmol) and the suspension was stirred at r.t. for 6 h (became a clear solution). The solution was concentrated in vacuo to give a white solid which was triturated with ether and filtered. The white solid was collected and dried under high vacuum to give the desired product.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto give a white solid which
  3. customwas triturated with ether
  4. filtrationfiltered
  5. customThe white solid was collected
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-694c38871b384cdaa1f1e7311df22c69
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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