Acetyl chloride → (2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-(hydroxymethyl)-4-(2-nitroethyl)-5,6-dihydropyridine-1 (2H)-carboxylate

HRID 627233Notes

Reaction equation

HRID 627233 reaction equation
[CH2:1]([O:8][N:9]([C@H:22]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:25]([CH2:35][O:36][Si](C(C)(C)C)(C)C)[CH:24]=[C:23]1[CH2:44][CH2:45][N+:46]([O-:48])=[O:47])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C>CO>[CH2:1]([O:8][N:9]([C@H:22]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:25]([CH2:35][OH:36])[CH:24]=[C:23]1[CH2:44][CH2:45][N+:46]([O-:48])=[O:47])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:11])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 89852745(2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-(2-nitroethyl)-5,6-dihydropyridine-1(2H)-carboxylate2×

Product 1

HCID 89852666(2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-(hydroxymethyl)-4-(2-nitroethyl)-5,6-dihydropyridine-1 (2H)-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-(2-nitroethyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 220, 5 g, 7.07 mmol) was taken up in methanol (150 mL) cooled to 0° C. and acetyl chloride (0.075 mL, 1.06 mmol) added. The reaction mixture was stirred for 3 hours at 0° C. The solvent was removed in vacuo and the residue was taken up in EtOAc, washed with saturated sodium bicarbonate, dried over Na2SO4, filtered and concentrated to afford the title compound as an oil (4.1 g, 98%).

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-16729d9b45454368b41140630dacaf44
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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