Hydrochloric Acid → (Z)-2-(2-Boc-aminothiazole-4-yl-)-2-trityloxyiminoacetic acid

HRID 1707439Notes

Reaction equation

HRID 1707439 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:18]/[OH:19])/[C:15]([OH:17])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:26]1([C:32](Cl)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:18]/[O:19][C:32]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)/[C:15]([OH:17])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6456Trityl chlorideHCID 11430Potassium CarbonateHCID 10085439(2Z)-2-hydroxyimino-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]acetic Acid

Product 1

HCID 10459636(Z)-2-(2-Boc-aminothiazole-4-yl-)-2-trityloxyiminoacetic acidYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-hydroxyiminoacetic acid (86.3 g: 0.30 Mol.) in dimethylformamide (600 ml) are added potassium carbonate (92 g: 0.67 Mol.) and triphenylmethyl chloride (100 g: 0.36 Mol.), and the mixture is stirred at room temperature for 3 days. The reaction mixture is poured into a mixture of concentrated hydrochloric acid (111 ml) and ice water (1500 ml) and extracted with ethyl acetate. The extract is washed with water, aqueous 5% sodium hydrogen carbonate, 2% hydrochloric acid and brine, dried over sodium sulfate, and concentrated. The residue is crystallized from dichloromethane to give (Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetic acid (144 g) as colorless crystals. Yield: 91%. mp. 157° to 158° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water, aqueous 5% sodium hydrogen carbonate, 2% hydrochloric acid and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is crystallized from dichloromethane

Sources & evidence

ORD record
ord-41711c90c62a421db2ea9798f69f07b3
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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