Diethyl Ether → 2-(2-Amino-1,3-thiazol-4-yl)-2-[3-(3,4-diacetoxybenzoyl)carbazoyl]methoxyiminoacetic acid tert-butyl ester hydrochloride

HRID 1383125Notes

Reaction equation

HRID 1383125 reaction equation
[C:1]([O:5][C:6](=[O:21])[C:7]([C:15]1[N:16]=[C:17]([NH2:20])[S:18][CH:19]=1)=[N:8][O:9][CH2:10][C:11](=[O:14])[NH:12][NH2:13])([CH3:4])([CH3:3])[CH3:2].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[C:34]([O:37][C:38]1[CH:39]=[C:40]([CH:44]=[CH:45][C:46]=1[O:47][C:48](=[O:50])[CH3:49])[C:41]([Cl:43])=[O:42])(=[O:36])[CH3:35].CCOCC>C(Cl)Cl.CO>[ClH:43].[C:1]([O:5][C:6](=[O:21])[C:7]([C:15]1[N:16]=[C:17]([NH2:20])[S:18][CH:19]=1)=[N:8][O:9][CH2:10][C:11](=[O:14])[NH:12][NH:13][C:41](=[O:42])[C:40]1[CH:44]=[CH:45][C:46]([O:47][C:48](=[O:50])[CH3:49])=[C:38]([O:37][C:34](=[O:36])[CH3:35])[CH:39]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 140969484-(Chlorocarbonyl)-1,2-phenylene diacetateHCID 540155642-(2-Amino-1,3-thiazol-4-yl)-2-carbazoylmethoxyiminoacetic acid tert-butyl ester

Product 1

HCID 867427652-(2-Amino-1,3-thiazol-4-yl)-2-[3-(3,4-diacetoxybenzoyl)carbazoyl]methoxyiminoacetic acid tert-butyl ester hydrochlorideYield 98.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In 50 ml of methylene chloride was suspended 6.12 g (19.4 mmole) of 2-(2-amino-1,3-thiazol-4-yl)-2-carbazoylmethoxyiminoacetic acid tert-butyl ester, and to the suspension was added 20.8 g (102.3 mmole) of N,O-bis(trimethylsilyl)acetamide to form a solution. To the ice-cooled solution was added 5.467 g (21.3 mmole) of 3,4-diacetoxybenzoic acid chloride and the mixture was stirred for 2 hours under ice-cooling. The resulting mixture was poured into 800 ml of ether and to the mixture was added a small amount of methanol while stirring. Resulting precipitates were collected by filtration, washed with ether and then dried to obtain 10.2 g of 2-(2-amino-1,3-thiazol-4-yl)-2-[3-(3,4-diacetoxybenzoyl)carbazoyl]methoxyiminoacetic acid tert-butyl ester hydrochloride. (Yield: 98.2%)

Workup

  1. customto form a solution
  2. temperaturecooling
  3. stirringwhile stirring
  4. customResulting
  5. customprecipitates
  6. filtrationwere collected by filtration
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-0812456c98204f58a03d573037679d5c
Source dataset
uspto-grants-1989_02
Patent number
US04808711

Reaction notes

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