Pyridine → HCID 20162855, compound

HRID 1905651Notes

Reaction equation

HRID 1905651 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C:13]1([S:25][CH3:26])[CH2:16][N:15]([Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C:14]1=[O:24].C(N(CC)CC)C.N1C=CC=CC=1.[O:40]([CH2:47][C:48](Cl)=[O:49])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>ClCCl>[Si:17]([N:15]1[CH2:16][C:13]([S:25][CH3:26])([NH:12][C:48](=[O:49])[CH2:47][O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:14]1=[O:24])([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 14356378HCID 14356378, compound

Product 1

HCID 20162855HCID 20162855, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of (23) (830)mg) in dry dichloromethane (20 ml) at -10° C. was treated with triethylamine (220 mg) and pyridine (172 mg), followed by a solution of phenoxyacetyl chloride (372 mg) in dry dichloromethane (~4 ml). The mixture was washed with very dilute HCl, followed by brine. The organic phase was dried and the solvent evaporated. Chromatography on silica yet gave the product (24) (730 mg). νmax (CHCL3) 3400, 1745, and 1690 cm-1 ; δppm (CDCl3) (90 MHz) 0.25 and 0.27 (boths, together 6H), 0.98 (S, 9H), 2.22 (S, 3H), 3.36 and 3.81 (ABq, 2H, J 7.0 Hz), 4.50 (S, 2H), 6.80 to 7.50 (m, 6H).

Workup

  1. washThe mixture was washed with very dilute HCl
  2. customThe organic phase was dried
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-c343dd2632774a4b8eb326113f810fb6
Source dataset
uspto-grants-1987_03
Patent number
US04647558

Reaction notes

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