Ammonia → HCID 18397290, compound

HRID 376859Notes

Reaction equation

HRID 376859 reaction equation
C([S:4][CH2:5][CH2:6][C:7]([N:9]1[C@@H:13]([C:14]([OH:16])=[O:15])[C:12]([CH3:18])([CH3:17])[S:11][CH2:10]1)=[O:8])(=O)C.N>O.C(OCC)(=O)C>[SH:4][CH2:5][CH2:6][C:7]([N:9]1[C@@H:13]([C:14]([OH:16])=[O:15])[C:12]([CH3:18])([CH3:17])[S:11][CH2:10]1)=[O:8]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 18397283HCID 18397283, compound

Product 1

HCID 18397290HCID 18397290, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The S-acetyl derivative E7 (70 mg, 0.24 mmol) was dissolved in water (0.6 ml) and concentrated aqueous ammonia (0.4 ml, sp.gr. 0.88) and stirred at room temperature for 1 hour. The reaction mixture was diluted in ethyl acetate and washed with sufficient dilute hydrochloric acid to acidify the aqueous phase. The two-phase system was treated with saturated brine and the organic layer separated, washed with further brine, dried over sodium sulphate and evaporated to afford the title compound as a colourless oil (60 mg, 100%). νmax (CHCl3) 1744, 1722, 1651, 1410 cm-1. δH (CDCl3) 1.52 (3 H, s), 1.60 (3 H, s), 1.81 (1 H, t, J 8.2 Hz), 2.7-2.9 (4 H, overlapping m), 4.55 (1 H, s), 4.75 (2 H, ABq) ppm. EIMS M+ 249.0496; required for C9H15NO3S2, 249.0493.

Workup

  1. washwashed with sufficient dilute hydrochloric acid
  2. additionThe two-phase system was treated with saturated brine
  3. customthe organic layer separated
  4. washwashed with further brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-f41edd09c56746cba59669c23a9e56d5
Source dataset
uspto-grants-2000_02
Patent number
US06022885

Reaction notes

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