Acetyl chloride → HCID 70984521, compound

HRID 928037Notes

Reaction equation

HRID 928037 reaction equation
[CH2:1]([N:8]([CH2:19][C@H:20]1[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]1)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C>CO>[NH:22]1[CH2:23][CH2:24][C@H:20]([CH2:19][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9](=[O:10])[O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:21]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86713351HCID 86713351, compound2×

Product 1

HCID 70984521HCID 70984521, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl (S)-3-[N-benzyl-N-(benzyloxycarbonyl)aminomethyl]pyrrolidine-1-carboxylate (Intermediate 167, 11 g) was added dropwise to a solution of acetyl chloride (15 g) in methanol (50 mL) and the resultant mixture was stirred at room temperature overnight. The mixture was concentrated under vacuum and the residue was purified by HPLC (C18) to give benzyl N—((S)-pyrrolidin-3-ylmethyl)-N-benzylcarbamate (8.0 g) as an off white solid which was used without further characterisation.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was purified by HPLC (C18)

Sources & evidence

ORD record
ord-26bba1bcc1f24e878c8925164a35970a
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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