Triethylamine → HCID 20162889, compound

HRID 246863Notes

Reaction equation

HRID 246863 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.[N+:34]([C:37]1[CH:55]=[CH:54][C:40]([CH2:41][O:42][C:43]([CH:45]([C:49]2[CH:53]=[CH:52][S:51][CH:50]=2)[C:46](Cl)=[O:47])=[O:44])=[CH:39][CH:38]=1)([O-:36])=[O:35]>ClCCl>[Si:17]([N:15]1[CH2:16][C:13]([S:25][CH3:26])([NH:12][C:46](=[O:47])[CH:45]([C:43]([O:42][CH2:41][C:40]2[CH:54]=[CH:55][C:37]([N+:34]([O-:36])=[O:35])=[CH:38][CH:39]=2)=[O:44])[C:49]2[CH:53]=[CH:52][S:51][CH:50]=2)[C:14]1=[O:24])([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14356378HCID 14356378, compoundHCID 20162886HCID 20162886, compound

Product 1

HCID 20162889HCID 20162889, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (23) (418 mg) in dry dichloromethane (10 ml) containing triethylamine (222 mg) at 0° C. was treated with a solution of 2-(p-nitrobenzyloxycarbonyl)-2-thien-3-ylacetylchloride (407 mg) in dry dichloromethane (5 ml). The mixture was stirred at 0° C. for 15 minutes, then allowed to warm to room temperature. After 1 hour the mixture was washed successively with sat. NaHCO3, water, dilute HCl, water and brine. The organic phase was dried (MgSO4), filtered and evaporated. Chromatography of the residue on silica gel gave the product (39) (496 mg) as a foam. νmax(CHCl3) 3390, 1745, 1685, 1525 and 1350 cm-1 ; δppm (CDCl3) (90 MHz) 0.97 (s, 9H), 2.18 and 2.21(both s, together 3H), 3.31 and 3.73 and, 3.33 and 3.75 (both ABq, together 2H, J7 Hz), 4.79 and 4.81 (both s, together 1H), 5.31(s, 2H), 7.01 (s, 1H, exch. D2O), 7.10 to 7.60 (m, 5H), 8.22(s, 2H, J9 Hz), (--Si(CH3)2 obscured by TMS).

Workup

  1. temperatureto warm to room temperature
  2. washAfter 1 hour the mixture was washed successively with sat. NaHCO3, water, dilute HCl, water and brine
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-e91b791538cc425588c18f3e26b7d4a8
Source dataset
uspto-grants-1987_11
Patent number
US04704385

Reaction notes

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