Pyridine → HCID 57254020, compound

HRID 2084965Notes

Reaction equation

HRID 2084965 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 6 h 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-106cb3019b444e69bda74c2b48cab7e2
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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