Pyridine → HCID 86594896, compound

HRID 1903233Notes

Reaction equation

HRID 1903233 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]([O:16][C:17]([NH:19][C@@H:20]([CH3:23])[CH2:21][OH:22])=[O:18])([CH3:15])([CH3:14])[CH3:13].N1C=CC=C[CH:25]=1>>[C:12]([O:16][C:17]([NH:19][C@@H:20]([CH3:23])[CH2:21][O:22][S:7]([C:4]1[C:5]([CH3:25])=[CH:6][CH:1]=[CH:2][CH:3]=1)(=[O:8])=[O:9])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 86594896HCID 86594896, compound

Procedure

p-Toluenesulphonyl chloride (4.2 g.) was added to a solution of (S)-2-t-butoxycarbonylamino-1-propanol (3.5 g.) in pyridine (10 ml.) at 0°. The mixture was kept at 0°-5° for 20 hr. and then poured into ice-water (200 ml.) and extracted with diethyl ether (3×50 ml.). The diethyl ether extract was washed successively with 1 M-hydrochloric acid (50 ml.), saturated sodium carbonate solution (50 ml.) and brine (50 ml.), and then dried (MgSO4). The solvent was evaporated and the residue was crystallised from ethyl acetate-petroleum ether to give (S)-2-t-butoxycarbonylamino-1-toluenesulphonyloxypropane, m.p. 73°-4°.

Workup

  1. extractionextracted with diethyl ether (3×50 ml.)
  2. extractionThe diethyl ether extract
  3. washwas washed successively with 1 M-hydrochloric acid (50 ml.), saturated sodium carbonate solution (50 ml.) and brine (50 ml.)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue was crystallised from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-bc4b0b2921424821a8caed6af33fa075
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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