Trityl chloride → HCID 88197801, compound

HRID 619232Notes

Reaction equation

HRID 619232 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:15])=[C:5](/[C:7](=[N:13]/[OH:14])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>CN(C)C=O>[OH:14]/[N:13]=[C:7](/[C:5]1[N:6]=[C:2]([NH:1][C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[S:3][C:4]=1[CH3:15])\[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 88198446ethyl (2Z)-2-(2-amino-5-methyl-1,3-thiazol-4-yl)-2-hydroxyiminoacetate

Product 1

HCID 88197801HCID 88197801, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 2-(2-amino-5-methylthiazol-4-yl)-2-(Z)-(hydroxyimino)acetate (8.73 g) in dimethylformamide (60 ml) was treated portionwise with trityl chloride (11.7 g) and dropwise with triethylamine (6.4 ml). The reaction mixture was quenched by water and extracted with ethyl acetate. The combined extracts were washed with water and brine, and were dried with magnesium sulfate. The solvent was removed under reduced pressure to afford ethyl 2-(Z)-hydroxyimino-2-(5-methyl-2-tritylaminothiazol-4-yl)acetate (16.15 g).

Workup

  1. customThe reaction mixture was quenched by water
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialwere dried with magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4661c62ceb434d08b1f4fe47d13c92f2
Source dataset
uspto-grants-1999_09
Patent number
US05958914

Reaction notes

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