Trityl chloride → (Z)-alpha-((2-(tert-Butoxy)-1,1-dimethyl-2-oxoethoxy)imino)-2-(tritylamino)thiazol-4-acetic acid

HRID 323879Notes

Reaction equation

HRID 323879 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][C:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH3:15])[CH3:14])/[C:8]([OH:10])=[O:9])[N:6]=1.C(N(CC)CC)C.[C:30]1([C:36]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)Cl)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[C:19]([O:18][C:16]([C:13]([O:12]/[N:11]=[C:7](/[C:5]1[N:6]=[C:2]([NH:1][C:36]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[S:3][CH:4]=1)\[C:8]([OH:10])=[O:9])([CH3:14])[CH3:15])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 6242497(alphaZ)-2-Amino-alpha-((2-(1,1-dimethylethoxy)-1,1-dimethyl-2-oxoethoxy)imino)-4-thiazoleacetic acid

Product 1

HCID 11039088(Z)-alpha-((2-(tert-Butoxy)-1,1-dimethyl-2-oxoethoxy)imino)-2-(tritylamino)thiazol-4-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

To a suspension of (Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxycarbonylprop-2-oxyimino) acetic acid (monoblocked acid) (100 g) prepared as in Example 1 in methylene chloride (1.74 lt) is added triethylamine (33.76 g) slowly at 5-10° to obtain a clear solution. Add triphenylchloromethane (118.5 g) at 5-10° and then mass temperature is raised to 36-38°. The resulting reaction mixture is stirred for 6 hours. It is then cooled to 20-25° and washed with DM water. The organic layer is concentrated and toluene is added to the residue. The resulting slurry is cooled to 20-25° C., the product is filtered, washed with toluene and dried under reduced pressure at 40-45° C. Yield 171 g (98.5% of theory), water <0.2% w/w, assay 96-97% w/w, methylene chloride 2-2.5% w/w and toluene 1-2% w/w.

Workup

  1. customto obtain a clear solution
  2. customThe resulting reaction mixture
  3. temperatureIt is then cooled to 20-25°
  4. washwashed with DM water
  5. concentrationThe organic layer is concentrated
  6. additiontoluene is added to the residue
  7. filtrationthe product is filtered
  8. washwashed with toluene
  9. customdried under reduced pressure at 40-45° C

Sources & evidence

ORD record
ord-76e064d125964f48a78c852410c2ef04
Source dataset
uspto-grants-2001_04
Patent number
US06214997B1

Reaction notes

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