Acetyl chloride → HCID 86713350, compound

HRID 928036Notes

Reaction equation

HRID 928036 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH:5]1[CH2:9][CH2:8][C@H:7]([CH2:10][N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:6]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([N:5]1[CH2:9][CH2:8][C@H:7]([CH2:10][N:11]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 70984521HCID 70984521, compound2×

Product 1

HCID 86713350HCID 86713350, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (2.86 g) was added to a stirred solution of benzyl N—((S)-pyrrolidin-3-ylmethyl)-N-benzylcarbamate (Intermediate 166, 5.9 g) and triethylamine (3.68 g) in DCM (80 mL) with ice cooling. The resultant mixture was stirred at room temperature for 2 hours then concentrated under vacuum. The residue was treated with saturated aqueous sodium bicarbonate and extracted with ethyl acetate, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with ethyl acetate to give benzyl N—((S)-1-acetylpyrrolidin-3-ylmethyl)-N-benzylcarbamate (4.2 g) as a yellow oil.

Workup

  1. concentrationthen concentrated under vacuum
  2. additionThe residue was treated with saturated aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-acd4eeaf242b48f0bdee8d0db0f79aeb
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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