Pyridine → HCID 57254020, compound

HRID 1976491Notes

Reaction equation

HRID 1976491 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[C:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:24][CH2:23][S:22][C:21]([CH3:26])([CH3:25])[C@@H:20]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])(=[O:18])=[O:17])=[CH:12][CH:11]=1.[C:34](OC(=O)C)(=[O:36])[CH3:35].N1C=CC=CC=1>>[C:34]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[C:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:24][CH2:23][S:22][C:21]([CH3:26])([CH3:25])[C@@H:20]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])(=[O:18])=[O:17])=[CH:12][CH:11]=1)(=[O:36])[CH3:35]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 57047881HCID 57047881, compound

Product 1

HCID 57254020HCID 57254020, compoundYield 97.1%

Procedure

A mixture of 0.452 g (0.908 mmol) of tert-butyl (3S)-4-({4-[(7-hydroxy-2-heptynyl)oxy]phenyl}sulfonyl)-2,2-dimethyl-3-thiomorpholinecarboxylate, 2.6 mL (27 mmol) of acetic anhydride and 0.22 mL (2.7 mmol) of pyridine was stirred at room temperature for 6h and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate:hexanes (1:5 ) to provide 0.476 g (97%) of tert-butyl (3S)4-[(4-{[7-(acetyloxy)2-heptynyl]oxy}phenyl)sulfonyl]-2,2-dimethyl-3-thiomorpholinecarboxylate as a colorless oil. Electrospray Mass Spec: 540.0 (M+H)+

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed on silica gel eluting with ethyl acetate:hexanes (1:5 )

Sources & evidence

ORD record
ord-8804d2c41f544c1ca54d8f3290ce90f2
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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