Triethylamine → HCID 20162889, compound

HRID 1905655Notes

Reaction equation

HRID 1905655 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.

Workup

  1. temperatureto warm to room temperature
  2. washAfter 1 hour the mixture was washed successively
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3ffcf09b3cac4d29b223e7efc301e48b
Source dataset
uspto-grants-1987_03
Patent number
US04647558

Reaction notes

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